Tag: M.W=200-300

Application of 460-37-7, A common heterocyclic compound, 460-37-7, name is 1,1,1-Trifluoro-3-iodopropane, molecular formula is C3H4F3I, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Method A: 1.8 g (7.13 mmol) of the compound from Ex. 49A and 3.49 g (10.7 mmol) of caesium carbonate were stirred in 15 ml of DMF at RT for 10 min, before 1.3 ml (10.7 mmol) of 1,1,1-trifluoro-3-iodopropane were added. Subsequently, the reaction mixture was stirred at a temperature of 100 C. in a microwave oven (Biotage Initiator with dynamic control of irradiation power). After 2 h, a further 167 mul (1.43 mmol) of 1,1,1-trifluoro-3-iodopropane were added and the heating was continued for 30 min. After cooling to RT, the mixture was diluted with about 75 ml of ethyl acetate and washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate, the mixture was filtered and the filtrate was evaporated to dryness. The crude product was purified by MPLC (Biotage cartridge, 100 g of SNAP KP-Sil silica gel, eluent: cyclohexane/ethyl acetate 1:2). After concentration and drying, a mixture of N- and O-alkylated product was obtained, from which it was possible to obtain the N-alkylated main product in solid form by stirring with a mixture of 30 ml of pentane and 2 ml of dichloromethane. Further N-alkylated product was obtained from the concentrated mother liquor from the stirring by means of preparative HPLC (Method 8). After concentration of the product fractions and drying under high vacuum, together with the solids from the stirring, 1.86 g (74% of theory) of the title compound were obtained.

The synthetic route of 460-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HAeRTER, Michael; KOSEMUND, Dirk; DELBECK, Martina; KALTHOF, Bernd; WASNAIRE, Pierre; SUessMEIER, Frank; LUSTIG, Klemens; (369 pag.)US2018/65981; (2018); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13194-68-8, name is 4-Iodo-2-methylaniline, A new synthetic method of this compound is introduced below., name: 4-Iodo-2-methylaniline

A solution of 4-iodo-2-methylaniline (10.0 g, 42.9 mmol) in glacial acetic acid (400 mL) was treated with a solution of NaNO2 (2.96 g, 42.9 mmol) in water (10 mL). After stirring for 6 hours, the mixture was concentrated to dryness and dissolved in ethyl acetate (EtOAc). Filtration through a pad of silica gel (EtOAc) provided the title compound (10.4 g, 99%) as a deep purple solid: ESI MS m/z 245 [M+H]+.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; AMR TECHNOLOGY, INC.; US2009/82359; (2009); A1;,
Iodide – Wikipedia,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 914225-70-0, name is 1-(5-Fluoro-2-iodophenyl)ethanone, A new synthetic method of this compound is introduced below., Safety of 1-(5-Fluoro-2-iodophenyl)ethanone

Under a nitrogen atmosphere, a solution of compound 1 (2.6 g, 10 mmol) in methanol (50 mL) was cooled in an ice-water bath, into which NaBH4 (0.38 g, 10 mmol) was poured slowly, and continued to react at 0C for 5 minutes. 0.5M HCl solution was added dropwise slowly until no bubbles appeared in the reaction system. The reaction solution was adjusted to pH > 7 with saturated sodium bicarbonate solution, and extracted with ethyl acetate to obtain 2.6 g of a white solid product with a yield of 99%. LC-MS (APCI): m/z = 267 (M+1)+; 1H NMR (300 MHz, CDCl3)(delta/ppm)7.76-7.71 (m, 1H), 7.35-7.31 (m, 1H), 6.78-6.72 (m, 1H), 5.05-4.99 (m, 1H), 1.45 (d, J=6.0 Hz, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Shenzhen Targetrx, Inc.; WANG, Yihan; LI, Huanyin; (30 pag.)EP3415518; (2018); A1;,
Iodide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 124700-40-9, name is 2-Fluoro-4-iodobenzoic acid, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 124700-40-9, category: iodides-buliding-blocks

a. Methyl 2-fluoro-4-iodobenzoate (2). A modified procedure of Kakuta and co-workers was followed.2 2-Fluoro-4-iodobenzoic acid (5.35 g, 20.1 mmol) was dissolved in methanol (30 mL, 741 mmol) was added thionyl chloride (2.6 mL, 35.8 mmol), dropwise at 0 C with stirring. The reaction solution was then refluxed in an oil bath at 85 C for 1 hr. Excess methanol was removed in vacuo, and benzene (20 mL) was added to the residue and then removed in vacuo. To the residue was added ethyl acetate (150 mL), and the organic layer was washed with saturated NaHCO3 (200 mL) and brine (60 mL) and then dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography (150 mL Si02, ethyl acetate:hexanes 1:48) to give 2 (5.3066 g, 94%) as a white crystalline solid, m.p. 76-78 C: 1H NMR (400 MHz, CDC13) 7.63 (t, J = 8.0, 1 H), 7.56 (dd, J= 8.4, 1.6, 1 H), 7.53 (dd, J = 10.0, 1.2, 1 H), 3.92 (s, 3H); ?3C NMR (100.6MHz, CDC13) 164.4, 164.3, 162.3, 159.7, 133.5, 133.4, 133.0, 126.5, 126.3, 118.2, 118.1, 99.8, 99.7, 52.5; JR (neat) n 2952, 1700, 1595, 1561 cm?; LC-FAB-MS (M)+ calcd for C8H6F102279.9397, found 279.9394.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-4-iodobenzoic acid, and friends who are interested can also refer to it.

Reference:
Patent; ARIZONA BOARD OF REGENTS ON BEHALF OF ARIZONA STATE UNIVERSITY; WAGNER, Carl; MARSHALL, Pamela; JURUTKA, Peter; WO2015/130973; (2015); A1;,
Iodide – Wikipedia,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 29289-13-2, name is 2-Iodo-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Iodo-4-methylaniline

General procedure: A mixture of 2-iodoaniline 1 (1 mmol), benzylamine 2 (1.2 mmol), sulfur powder (6 mmol), DABCO (2 mmol), Cu(OAc)2.H2O (0.02 mmol), and 1,10-phenanthroline (0.02 mmol) was stirredin DMSO (5 mL) at 100 C. After completion of the reaction as indicated by TLC, the mixture was cooled to room temperature, water (20 mL) was added, and then the aqueous solution was extracted with ethyl acetate (3 15 mL). The organic layers were combined, dried over anhydrous MgSO4, the filtrate was concentrated under vacuum and then the residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate (10:1 to 14:1) on silicagel to provide the desired product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 29289-13-2.

Reference:
Article; Wang, Rui; Ding, Yong-Liang; Liu, Hong; Peng, Shu; Ren, Jie; Li, Lei; Tetrahedron Letters; vol. 55; 4; (2015); p. 945 – 949;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 351003-36-6, These common heterocyclic compound, 351003-36-6, name is 2-Fluoro-5-iodobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 2-fluoro-5-iodobenzonitrile (479.2 mg, 1 .94 mmol) in tetrahydrofuran (4 mL) at -20 C was added isopropylmagesium chloride (2 N, 0.97 ml, 1 .94 mmol) and the mixture was stirred for 1 hour. Then, a solution of the product of Example 1 b (200 mg, 1 .29 mmol) in tetrahydrofuran (0.5 mL) was added and the mixture was stirred at -20 C for an additional 1 hour, then warmed to room temperature and stirred for 1 hour. The reaction was quenched with saturated aqueous ammonium chloride (10 mL) and the organics were extracted with ethyl acetate (10 mL x 3). The combined phase was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 50:1 ) to afford the title compound as a white solid (200 mg, Yield: 48%). Mp = 1 17.9- 1 19.2 C; Rf = 0.2 (10:1 ) petroleum ether/: ethyl acetate); H NMR (400 MHz, CDCIs) delta 7.69-7.67 (m, 1 H), 7.64-7.60 (m, 1 H), 7.15 (d, J = 8.6 Hz, 1 H), 5.06 (d, J = 4.8 Hz, 1 H),1 .85 (d, J = 5.6 Hz, 1 H), 1 .83-1 .76 (m, 1 H), 1 .64- 1 .60 (m, 1 H), 1 .50-1 .44 (m, 3 H), 1 .32-1 .23 (m, 2 H), 1 .14 (s, 3 H), 1 .06 (s, 3 H), 1 .00-0.89 (m, 1 H), 0.53 (d, J = 6.4 Hz, 3 H) ppm; (ESI +ve) m/z 276 (M +H+); [a]D27 0 = +27.1 (c = 0.31 , dichloromethane).

The synthetic route of 351003-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIKAM PHARMACEUTICALS, INC.; GARVEY, David, S.; WO2012/174064; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 13421-00-6,Some common heterocyclic compound, 13421-00-6, name is 5-Chloro-2-iodobenzoic acid, molecular formula is C7H4ClIO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a argon gas puged mixture of 2-iodo benzoic acids (1) (0.008 mol), Carbonyldiimidazole(0.008 mol) and K2CO3 (0.242 mol) in CH3CN (50 ml) was added Pd(OAc)2 (10 mol %) andstirred at 60 oC temperature for 12h. The reaction was monitored by TLC analysis. Aftercompletion of the reaction, the reaction mixture was poured carefully into ice-cold water (50mL) and the product was extracted with ethyl acetate (2 x 50 mL). The combined organic layerwas dried over anhydrous Na2SO4. After filtration, the solvent was evaporated under vacuum andthe crude product obtained was purified by column chromatography to afford the pure desiredproducts (2a-d).

The synthetic route of 13421-00-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Narsimha, Sirassu; Battula, Kumaraswamy; Vasudeva Reddy, Nagavelli; Synthetic Communications; vol. 47; 9; (2017); p. 928 – 933;,
Iodide – Wikipedia,
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Some common heterocyclic compound, 2142-70-3, name is 1-(2-Iodophenyl)ethanone, molecular formula is C8H7IO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 1-(2-Iodophenyl)ethanone

To a cooled (-40 C) stirred solution of TiC4 (11 mL of a 1.0 M sol in DCM, 11 mmol) in 5 mL of DCM was added dimethyl zinc (5.5 mL of a 2 N sol. in toluene, 11 mmol). After stirring for 10 min iodoacetophenone (1.23 g, 5.0 mmol) was added. After 2 h the reaction was warmed to 0 C and stirred for an addtional 1 h. The reaction was poured onto ice and extracted with ether. The organic phase was washed with water and sat NaHCO3. The organic phase was dried over magnesium sulfate, filtered, and dried under reduced pressure. The material was distilled using a kugelrohr (80 C at 0.1 mm) to obtain 1.0 g (76% yield) of a clear oil ; H NMR (300 MHz, CDCI3) 8 7.71 (t, J = 2.0 Hz, 1 H), 7.51 (dt, J = 7.7, 1.3 Hz, 1 H), 7.35 (app d, J = 7.7 Hz, 1 H), 7.03 (t, J = 7. 9 Hz, 1 H), 1.29 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2142-70-3, its application will become more common.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87752; (2005); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 620-05-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 620-05-3, name is (Iodomethyl)benzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure for the synthesis of diorganyl selenides and sulfides: commercially available Zn dust (33 mg, 0.5 mmol) and PhSeSePh/PhSSPh (0.5 mmol) and 15 muL of HCl 1N were added to BMIM-BF4 (0.5 mL) at room temperature under nitrogen. The mixture was allowed to stir for 2-3 min. Then corresponding organic halides (1 mmol) was slowly added. The reaction mixture was allowed to stir until the color change (monitored by TLC and assisted by visual observation). The mixture was then extracted with ether (3×15 mL), and the combined ether extract was washed with brine, dried (MgSO4), and evaporated to leave the crude product. Purification by column chromatography over silica gel (hexane/ethyl acetate 98:2) furnished the corresponding products.

The synthetic route of (Iodomethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Narayanaperumal, Senthil; Alberto, Eduardo E.; Gul, Kashif; Kawasoko, Cristiane Yuriko; Dornelles, Luciano; Rodrigues, Oscar E.D.; Braga, Antonio Luiz; Tetrahedron; vol. 67; 25; (2011); p. 4723 – 4730;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 25309-64-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 25309-64-2, name is 1-Ethyl-4-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of aryl halides (2.0 mmol) and thiourea (1.2 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 110 C for 15 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product in excellent yields.Recycling of the catalyst:after the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (2.0 mL) was added and CuO was removed by centrifugation. After each cycle, the catalyst was recovered by simple centrifugation, washing with deionized water and ethyl acetate and then drying in vacuo. The recovered nano CuO was used directly in the next cycle.Data of representative examples:Dip-tolylsulfane (Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Table 3, entry 3): yellow oil;1H NMR (200 MHz, CDCl3, TMS): delta = 7.21 (d, 4H, J = 8.0 Hz), 7.06 (d, 4H, J = 8.0 Hz), 2.32 (s, 6H); 13C NMR (50 MHz, CDCl3, TMS): delta = 136.7, 132.81, 131.0, 129.8, 96.1.Bis(4-ethylphenyl)sulfane (Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Table 3, entry 4): colorless oil; 1HNMR (300 MHz, CDCl3, TMS): delta = 7.21(d, 4H, J = 7.8 Hz), 7.07 (d, 4H, J = 7.8 Hz), 2.62-2.52 (m, 4H), 1.26 (t, 6H, J = 7.8 Hz);13C NMR (75 MHz, CDCl3, TMS): delta = 143.1, 132.7, 131.0, 128.6, 28.3, 15.4; mass (EI): m/z 242 [M]+; Anal. calcd for: (C16H18S) C, 79.29; H, 7.49; S, 13.23; found: C,79.22; H,7.42; S,13.19.Bis(3-nitrophenyl)sulfane (Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.Table 3, entry 7): pale yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 8.19-8.15 (m, 4H), 7.65 (d, 2H, J = 8.3 Hz), 7.55 (t, 2H, J = 8.3 Hz); 13C NMR (75 MHz, CDCl3, TMS): delta = 148.8, 136.7, 130.7, 125.6, 122.7; mass (EI): m/z 276 [M]+; Anal. calcd for: (C12H8N2O4S) C, 52.17; H, 2.92; S, 11.61; N, 10.14; found: C, 52.12; H, 2.86; S, 11.55; N, 10.9.4,4′-Thiodianiline (Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Table 3, entry 11): brown solid; mp 104-105 C; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.10 (d, 4H, J = 8.68 Hz), 6.52 (d, 4H, J = 8.68 Hz), 3.51 (br s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 145.5, 133.8, 132.6, 124.8, 115.6; mass (EI): m/z 216 [M]+; Anal. calcd for: (C12H12N2S) C, 66.63; H, 5.59; N, 12.95; S, 14.82; Found: C, 66.61; H, 5.58; N, 12.92; S, 14.81.Dithiophen-3-ylsulfane (Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Table 3, entry 15): yellow oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 7.31-7.25 (m, 2H), 7.17-7.11(m, 2H), 6.96-6.94 (m, 2H); 13C NMR (75 MHz, CDCl3, TMS): delta = 129.6, 126.4, 124.7; mass (EI): m/z 197 [M]+; Anal. calcd for: (C8H6S3) C, 48.45; H, 3.05; S, 48.50; found: C,48.42; H,3.02; S,48.47.Dipyrimidin-5-ylsulfane (Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; found: C, 50.45; H, 3.13; N, 29.41; S, 16.81.Table 3, entry 17): colorless oil; 1H NMR (300 MHz, CDCl3, TMS): delta = 9.15 (s, 2H), 8.74(s, 4H); 13C NMR (75 MHz, CDCl3, TMS): delta = 158.6, 157.7, 129.8; mass (EI): m/z 190 [M]+; Anal. calcd for: (C8H6N4S) C, 50.51; H, 3.18; N, 29.45; S, 16.86; f…

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Ethyl-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Reddy, K. Harsha Vardhan; Reddy, V. Prakash; Shankar; Madhav; Anil Kumar; Nageswar; Tetrahedron Letters; vol. 52; 21; (2011); p. 2679 – 2682;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com