Iodides-buliding-blocks

A common compound: 35453-19-1, name is 5-Amino-2,4,6-triiodoisophthalic acid, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 35453-19-1

A. Preparation of 5-Amino-2,4,6-triiodoisophthaloyl Chloride (2) STR1 5-Amino-2,4,6-triiodoisophthalic acid (6.73 Kg, 12.04 mol) 1 was charged and EtOAc was added. SOCl2 (5.73 Kg, 48.17 mol) was added to the slurry in one portion and the mixture was heated at reflux for 4 hours. After the reaction, 24.2 L of unreacted SOCl2 and the solvent were distilled (64-77, 7 hrs. distillation time). The product started to precipitate when the reaction solution cooled to 55; the slurry was stirred overnight, allowing it to cool to room temperature. The solids were collected, washed with cold EtOAc (5, 3.8 L), suction-dried for 3 hours and air-dried at room temperature to give the desired product 2 (3.525 kg, 49.2% yield). The filtrate (about 25 L) was distilled to a volume of 15 L and cooled to 2 overnight. The precipitated product was collected, washed with cold EtOAc (5, 1.5 L), suction-dried and air-dried to give a second crop of the product 2 (0.83 kg, 11.6% yield). The two crops of the product were combined, 4.355 kg (60.8% yield). The product showed one spot by tlc analysis (C6 H5 CH3 /CH3 OH; 9/1).

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, 35453-19-1, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mallinckrodt, Inc.; US4396598; (1983); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

83863-33-6, 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. 83863-33-6, name is 5-Iodo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

PREPARATION 21 N-(4-Iodo-2-methylphenyl)acetamide In the manner of Preparation 5, 10 g (0.043 mol) of 5-iodo-2-methylaniline was converted into the title compound: yield 11.1 g (94%); m.p. 182-183 C. Analysis calculated for C9 H10 INO: C, 39.29; H, 3.66; N, 5.09%. Found: C, 39.61; H, 3.77; N, 4.96%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Pfizer Inc.; US4762838; (1988); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

18698-96-9, name is 2-(2-Iodophenyl)acetic acid, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 18698-96-9

(1-bis) A suspension of 2-iodophenyl acetic acid (Ig, 3.82 mmol), 4-bromobenzenethiol (0.722 g, 3.82 mmol), KOH (0.427 g, 7.63 mmol) and copper powder (24 mg, 0.38 mmol) in 2 mL of water, was allowed to react in microwave(conditions: 2x 6 min, 180 W, T max=100¡ãC, P max=100 psi) .The suspension obtained was dissolved in 2N aqueous solution of KOH and then filtered. The filtrate was acidified with IN aq. HCl; the white precipitate was filtered, dried in vacuo, purified by trituration with acetone to give the pure acid 1-bis as white solid (l.ldeltag, 94percent) .1H-NMR (CDCl3, 200MHz): 7.44 (d, J= 7Hz, IH); 7.36-7.26 (m, 5H); 7.01 (d, J= 8.4Hz, 2H); 3.86 (s, 2H). Anal. Calcd. for Ci4H11BrO2S (MW=323.2): C 52.03; H 3.43; Br 24.72; O 9.90; S 9.92.; Example 62- (2-biphenyl-4-ylthio) phenyl) acetic acid (19a), 2- (2- (4- methoxyphenylthio) phenyl) acetic acid (19b), 2- (2-biphenyl-4- ylthio) phenyl) -N-hydroxyacetamide (21a), N-hydroxy-2- (2- (4- methoxyphenylthio) phenyl) acetamide (21b) and 2- (2- (4- (but-2- iniloxy) phenylthio) phenyl) -N-hydroxyacetamide (21c); (16) Compound 16 was synthesized according to the procedure described for the preparation of 10, starting from o-iodophenylacetic acid (5 g, 19.08 mmol) and 4- bromobenzenethiol (2.4 g, 19.08 mmol) into 5 portions of 1 g each. The obtained suspension was collected and diluted in KOH 2N. The obtained suspension was filtered and acidified with HCl IN. The formed precipitate was brought to dryness under reduced pressure at 500C. There were recovered 4.37 g of 16 (88percent, white solid) . 1H-NMR (de-DMSO, 200MHz ) : 3 . 74 ( s , 2H) , 7 . 07 (d, J=8Hz , 2H) , 7 . 30 -7 . 42 (m, 4H) 7 . 4 9 (d, J=8Hz , 2H) , 12 . 34 (br . s , IH) .

Statistics shows that 18698-96-9 is playing an increasingly important role. we look forward to future research findings about 2-(2-Iodophenyl)acetic acid.

Reference:
Patent; BRACCO IMAGING SPA; UNIVERSITA DI PISA; WO2008/15139; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 64248-58-4, name is 1,2-Difluoro-4-iodobenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 64248-58-4

General procedure: General procedure for the synthesis of alpha-arylacetic acid tert-butyl esters: A Schlenk tube was charged with aryl iodide (1.0mmol), CuI (9.5mg, 0.05mmol), 2-picolinic acid (12mg, 0.10mmol), and cesium carbonate (978mg, 3.0mmol). The tube was evacuated and backfilled with argon three times before tert-butyl acetoacetate (2.0mmol) and 2mL of 1,4-dioxane was added. The tube was immersed in an oil bath, and the reaction mixture was stirred at the indicated temperatures for 33-48h. The cooled mixture was partitioned between ethyl acetate and saturated NH4Cl, the organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with PE/EA=20:1 to 3:1) to provide the desired alpha-arylacetic acid tert-butyl esters.

The synthetic route of 64248-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Conference Paper; Zhao, Duo; Jiang, Yongwen; Ma, Dawei; Tetrahedron; vol. 70; 20; (2014); p. 3327 – 3332;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

13194-68-8, A common heterocyclic compound, 13194-68-8, name is 4-Iodo-2-methylaniline, molecular formula is C7H8IN, 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.

General procedure: To a solution of NCTD (1, 1.0 g, 5.95 mmol) dissolved in tetrahydrofuran (THF, 10 mL)accompanied by triethylamine (TEA, 0.5 mL) as the acid-binding agent was added the correspondingaromatic amine (1 equiv., 5.95 mmol). When the reaction was complete after 14 h as checkedby TLC analysis, the solution was concentrated under reduced pressure and diluted with acetone(100 mL). The resulting filter cake was either recrystallized from methanol or purified by columnchromatography (MeOH/CH2Cl2, 1: 4, v/v) to afford the desired products II (1-36). The yields,physical properties, 1H-NMR, 13C-NMR, and HRMS-ESI of the target compounds II were as follows.

The synthetic route of 13194-68-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yang; Sun, Wenbo; Zha, Shunqing; Wang, Huan; Zhang, Yalin; McPhee, Derek J.; Molecules; vol. 20; 12; (2015); p. 21464 – 21480;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 627-32-7 name is 3-Iodo-1-propanol, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 627-32-7

Mitragynine (50.0 mg, 0.126 mmol) was dissolved in 3-iodopropanol (0.33 mL), and acetonitrile (CH3CN, 0.5 mL) was added to the solution. Under ice cooling, IBDA (40.5 mg, 0.126 mmol) was added in four portions at intervals of 4 minutes, and the mixture was stirred at room temperature for 1 hour in an argon atmosphere. The reaction liquid was poured into an ice-cold saturated sodium bicarbonate aqueous solution and extracted three times with ether. The extracted organic layers were washed with brine and dried over sodium sulfate, followed by evaporation of the solvent under reduced pressure and vacuum drying. Thus, a residue was obtained. The resultant residue was purified by medium pressure liquid chromatography (aminosilica gel, 30% ethyl acetate/n-hexane) to obtain an iodinated form represented by the following formula (V) (31.9 mg, 46% yield).Analysis data of the product are shown below. 1H-NMR (400 MHz, CDCl3) delta [ppm]: 7.45 (1H, s, H-17), 7.32 (1H, dd, J=8.0, 8.0 Hz, H-11), 7.24 (1H, d, J=7.6 Hz, H-12), 6.75 (1H, d, J=8.1 Hz, H-10), 3.87 (3H, s, 9-OCH3), 3.81 (3H, s, 17-OCH3), 3.71 (3H, s, 22-OCH3), 3.29 (2H, m, H2-1?), 3.05-2.98 (3H, overlapped, H-3, H-5, and H-15), 2.93 (2H, dd, J=5.3, 5.3 Hz, H2-3?), 2.89-2.70 (3H, overlapped, H-6, H-14, and H-21), 2.59 (1H, m, H-5), 2.45 (1H, dd, J=11.2, 2.6 Hz, H-21), 2.08-1.88 (3H, overlapped, H-14 and H2-2?), 1.74-1.56 (3H, overlapped, H-6, H-19, and H-20), 1.23 (1H, m, H-19), 0.82 (3H, dd, J=7.2, 7.2 Hz, H3-18).13C-NMR (100 MHz, CDCl3) delta [ppm]: 184.0 (C-2), 169.3 (C-22), 160.7 (C-17), 156.5 (C-9), 155.5 (C-13), 130.9 (C-11), 123.0 (C-8), 114.3 (C-12), 111.2 (C-16), 108.8 (C-10), 86.1 (C-7), 63.2 (C-1?), 62.2 (17-OCH3), 61.8 (C-3), 58.1 (C-21), 55.4 (9-OCH3), 51.3 (22-OCH3), 50.3 (C-5), 40.5 (C-20), 39.3 (C-15), 35.2 (C-6), 33.7 (C-2?), 25.9 (C-14), 18.9 (C-19), 12.8 (C-18), 3.7 (C-3?).UV (MeOH) lambdamax: 301.0, 245.5 (sh), 221.5 nm.CD (0.151 mM, MeOH, 24 C.), lambda nm (De): 345 (0), 309 (+2.8), 290 (0), 281 (-0.8), 275 (0), 258 (+4.8), 242 (0), 221 (-9.4), 210 (0). EI-MS (%) m/z: 582 (M+, 41), 397 (100).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Iodo-1-propanol, and friends who are interested can also refer to it.

Reference:
Patent; NATIONAL UNIVERSITY CORPORATION CHIBA UNIVERSITY; TAKAYAMA, Hiromitsu; (11 pag.)US2016/340352; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 660-49-1, name is 3-Fluoro-5-iodoaniline, molecular formula is C6H5FIN, 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. 660-49-1.

Production Example 342 benzhydrylidene-(3-fluoro-5-iodophenyl)-amine 0.75 g of the title compound (yellow oil) was obtained from 3.2 g of 3-fluoro-5-iodophenylamine (compound in Production Example 341) by the same reaction as in Production Example 336.1H-NMR (CDCl3) delta: 6.36-6.43(m, 1H), 6.86-6.92(m, 1H), 6.96-7.02(m, 1H), 7.08-7.16(m, 2H), 7.28-7.54(m, 6H), 7.68-7.76(m, 2H)

The synthetic route of 3-Fluoro-5-iodoaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; EP1382603; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

77317-55-6, These common heterocyclic compound, 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, 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.

Under N2, a suspension of methyl 2-amino-5-iodobenzoate (4) (2.77 g, 10 mmol), Pd(PPh3)4 (1.159 mg, 1 mmol), CuI (381 mg, 2 mmol), Et3N (4.2 mL, 30 mmol) and propargyl alcohol (1.75 ml, 30 mmol) in DMF (20 mL) was stirred at rt for 15 h. TLC analysis (petrol ether: ethyl acetate 1:1) indicated the fully consumption of starting material. The reaction was quenched with 200 ml sat. NaCl solution. Ethyl acetate: petrol ether 1:1 (200 ml) was added to the mixture and the aqueous layer was extracted with ethyl acetate:petrol ether 1:1 three times. After drying the combined organics over MgSO4, the solution was concentrated and purified by silica gel chromatography (petrol ether:ethyl acetate 80:20 to ethyl acetate), giving Compound 5 as a yellow oil (1.88 g, 92%). 1H NMR (CDCl3) delta 3.78 (s, 3H), 4.25 (s, 2H, CCH?2), 7.27-7.36 (m, 2H, arom.H), 7.58-7.65 (m, 1H, arom.H).

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 77317-55-6.

Reference:
Patent; Illumina, Inc.; Illumina Cambridge Limited; Wu, Xiaolin; Smith, Randall; Shieh, Peyton; Beierle, John M.; George, Wayne N.; Lawrence, Elliot John; Mao, Jie; Liu, Xiaohai; (62 pag.)US2019/352327; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 3032-81-3, name is 1,3-Dichloro-5-iodobenzene, This compound has unique chemical properties. The synthetic route is as follows., 3032-81-3

A 1000-mL flask equipped with overhead stirrer, condenser and thermometer was charged with l,3-dichloro-5-iodobenzene (99.0 g, 0.36 mol), 1,3-dimethyl 2-(3,5- dichlorophenyl)propanedioate (91.0 g, 0.69 mol), copper(I) iodide (4.0 g, 0.021mol), 2-picolinic acid (5.2 g, 0.042 mol) and cesium carbonate (350 g, 1.07 mol) in 1,4-dioxane (600 mL). The reaction mixture was heated under nitrogen to 90 C for 3 hours. The mixture was then cooled to 30 C, diluted with water (300 mL) and hexane (200 mL), and partitioned. The organic phase was washed with saturated aqueous ammonium chloride solution (200 mL) and concentrated under vacuum to a viscous oil. The resulting material was used directly in the next step.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; HOFFMANN, Christian; ZHANG, Wenming; CHEN, Yuzhong; WO2013/192035; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

55406-53-6, A common heterocyclic compound, 55406-53-6, name is 3-Iodoprop-2-yn-1-yl butylcarbamate, molecular formula is C8H12INO2, 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.

EXAMPLESA solution is prepared in Dowanol TPM (tripropylene glycol methyl ether), containing 10% by weight of iodopropargyl butylcarbamate, 5% by weight of Octasoligen-Cobalt 8 (Borchers, Langenfeld, Germany) and 5% by weight of the stabilizer specified in Table 1. The compositions are stored at 40 C. The amount of IPBC was determined by means of HPLC at the beginning and after two weeks.

The synthetic route of 55406-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Uhr, Hermann; US2009/36555; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com