Tag: M.W=100-200

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. 624-75-9, name is 2-Iodoacetonitrile, A new synthetic method of this compound is introduced below., 624-75-9

Step 2: Synthesis of 2-(2-chloro-6-morpholino-9H-purin-9-yl)acetonitrile (14c)To a solution of 13a (1.18 g, 4.94 mmol) in acetonitrile/DMSO (19:1) was added 2- iodoacetonitrile (0.71 mL, 9.87 mmol) and K2C03 (1.36 g, 9.87 mmol). The resulting mixture was heated at 60CC for 3 h. Then the solvents were removed in vacuo and water was added. The aqueous layer was extracted with DCM (x2) and the combined organic layers was washed with brine (xl), dried over MgSO4 and evaporated in vacuo. The crude oil was purified by flash chromatography(silica, 50% ethyl acetate in hexanes) to afford 14c (1.31 g, 95%) as pale brown solid.

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; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; WANG, Haishan; CHEN, Dizhong; SOH, Chang Kai; WO2015/137887; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 624-75-9, name is 2-Iodoacetonitrile, A new synthetic method of this compound is introduced below., 624-75-9

Cyanomethyl-trimethyl-phosphonium iodide (TJA01110); C5H11INP MW 243.03 Trimethylphosphine in THF (1M, 20.0 mL, 20.0 mmol) at 0 C under N2 (g) was diluted with anhydrous toluene (40 mL). Iodoacetonitrile (1.40 mL, 19.4 mmol) was added dropwise with vigorous stirring forming a white ppt. The mixture was allowed to warm to r. t. and left to stir for 40 h. The mixture was filtered and washed with toluene to give a white solid which was dried under vacuum. Recrystallisation (acetonitrile) provided the title compound as a white crystalline solid (3.23 g, 66 %), ?H NMR (300 MHz, DMSO-d6) No. 2.01-2.06 (9H, d, J= 15.3 Hz, P (CH3)3), (2H, d, J= 16.4 Hz, PCH2CN); 3?p NMR (121.5 MHz, DMSO-d6) No. 32.9.

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; STERIX LIMITED; WO2005/118560; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9, Adding a certain compound to certain chemical reactions, such as: 624-75-9, name is 2-Iodoacetonitrile, 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 624-75-9.

The compound obtained in Example 64 (4.6 g, 15.35 mmol) and potassium carbonate (10.6 g, 76.73 mmol) were added to acetone (100 mL) and refluxed for 2 hours. To this reaction mixture was dropwise added iodoacetonitrile (1.34 mL, 18.42 mmol), and refluxed over 2 hours. The acetone was removed by vacuum distillation, and the residue was treated in water (200 mL) and ethyl acetate (200 mL). The organic layer was dried over anhydrous magnesium sulfate and distillated in a vacuum. The concentrate was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:3 v/v) to afford a mixture of 2:1 of regioisomers as yellow oil. These two regioisomers (4.16 g, 80%) were used in the next reaction step without separation.Example 65-2Preparation of 4-(2-chloropyridin-5-yl)-5-(3-methoxy-5-methylphenyl)-pyrazol-1-yl)acetonitrile1H NMR (CDCl3) delta 2.28 (s, 3H), 3.66 (s, 3H), 5.16 (s, 2H), 6.71 (s, 2H), 6.84 (s, 1H), 7.24 (d, J=8.3 Hz, 1H), 7.49 (dd, J=2.3, 5.9 Hz, 1H), 7.70 (s, 1H, 8.32 (s, 1H); 13C NMR (CDCl3) delta 21.57, 39.89, 55.23, 110.80, 113.76, 115.28, 117.76, 121.47, 124.02, 127.24, 129.92, 132.57, 138.58, 140.12, 148.71, 149.92, 151.17, 159.69, 162.33.To a solvent mixture of THF and water (4:1, 10 mL) were added the mixture prepared in Example 65 (400 mg, 1.18 mmol), 2-acetylphenyl boronic acid (023 g, 1.42 mmol), dichlorobis(triphenylphosphine)palladium (II) (41 mg, 0.06 mmol) and potassium carbonate (0.16 g, 1.18 mmol). The reaction system was purged with nitrogen gas for 10 min, and stirred at 70 C. for 12 hours under nitrogen atmosphere. The reaction mixture was cooled at room temperature, washed with ice water (100 mL) and extracted with ethyl acetate (100 mL¡Á3). The organic extract was dried over anhydrous magnesium sulfate and distilled under vacuum. The residue was subjected to prep-TLC using a solvent mixture of ethyl acetate/hexane to purify the desired products.Purification yield by prep-TLC (silica gel, ethyl acetate-hexane, 1:2, v/v): (155 mg); m.p. 176-177 C.; 1H NMR (CDCl3) delta 2.25 (s, 3H), 2.28 (s, 3H), 3.70 (s, 3H), 5.14 (s, 2H), 6.72 (s, 1H), 6.76 (s, 1H), 6.89 (s, 1H), 7.44-7.65 (m, 6H), 7.70 (s, 1H), 8.54 (s, 1H); 13C NMR (CDCl3) delta 21.51, 30.58, 39.79, 55.19, 110.80, 113.82, 115.30, 118.66, 121.54, 121.89, 127.06, 127.63, 128.80, 128.96, 130.02, 130.36, 132.92, 136.56, 138.15, 139.93, 141.68, 148.55, 151.23, 155.76, 159.71, 204.39.

According to the analysis of related databases, 624-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEE, So Ha; Yoo, Kyung Ho; Oh, Chang Hyun; Han, Dong Keun; El-Deeb, Ibrahim Mustafa; Park, Byung Sun; Jung, Su Jin; US2011/15395; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9,Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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.

e) To a solution of 7-benzyloxymethyl-8-(4-hydroxyphenyl)-1,3-dipropyl-1,3,7-trihydropurine-2,6-dione (1 g, 2.2 mmol) in tetrahydrofuran (20 ml) was added potassium t-butoxide (0.28 g, 2.4 mmol), and the mixture stirred for 30 minutes at room temperature.iodoacetonitrile (0.38 g, 2.23 mmol) was then added, and the mixture stirred for 16 hours at room temperature.The solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate and passed through a silica gel plug, to provide 7-benzyloxymethyl-8-(4-cyanomethoxyphenyl)-1,3-dipropyl-1,3,7-trihydropurine-2,6-dione, a compound of formula (7)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodoacetonitrile, its application will become more common.

Reference:
Patent; Kalla, Rao; Perry, Thao; Elzein, Elfatih; Varkhedkar, Vaibhav; Li, Xiaofen; Ibrahim, Prabha; Palle, Venkata; Xiao, Dengming; Zablocki, Jeff; US2003/229106; (2003); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-76-0, name is 2-Iodoethanol, 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. 624-76-0

Example XII 2-(adamantan-1-ylamino)ethanol 1-Adamantylamine (1 g, 6.05 mmol) and 2-iodoethanol (1.20 g, 7.00 mmol) were dissolved in benzonitrile (2 ml). The mixture was heated at 120 C. for 12 h. After this, the precipitate was filtered off and carefully washed with petrolether (3*20 ml). The white solid was dissolved in DCM (30 ml) and washed with a saturated solution of Na2CO3 (3*50 ml). The organic layer was separated, dried with Na2SO4 and the solvent was removed under reduced pressure to yield the title compound as colourless oil (950 mg, 4.86 mmol, 80%). 1H NMR (250 MHz, CD2Cl2): delta=1.55 (m, 12H, -CH2-), 1.99 (bs, 5H, -CH- and over-lapping OH, NH), 2.65 (t, 2H, J=5 Hz, -CH2-), 3.44 (t, 2H, J=5.1 Hz, -CH2-); all spectroscopic data are in good agreement with previously reported ones, e.g. P. E. Aldrich, E. C. Herrmann, W. E. Meier, M. Paulshock, W. W. Prichard, J. A. Snyder, J. C. Watts, J. Med. Chem. 1971, 14, 535-543.

Statistics shows that 624-76-0 is playing an increasingly important role. we look forward to future research findings about 2-Iodoethanol.

Reference:
Patent; BASF SE; BASF (CHINA) COMPANY LIMITED; HASHMI, A., Stephen K.; LOTHSCHUeTZ, Christian; WO2012/56419; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9, The chemical industry reduces the impact on the environment during synthesis 624-75-9, name is 2-Iodoacetonitrile, I believe this compound will play a more active role in future production and life.

Cyanomethyl-trimethyl-phosphonium iodide (TJA01110) C5H11INP MW 243.03. Trimethylphosphine in THF (IM, 20.0 mL, 20.0 mmol) at 0 0C under N2 (g) was diluted with anhydrous toluene (40 mL). Iodoacetonitrile (1.40 mL, 19.4 mmol) was added dropwise with vigorous stirring forming a white ppt. The mixture was allowed to warm to r.t. and left to stir for 40 h. The mixture was filtered and washed with toluene to give a white solid which was dried under vacuum. Recrystallisation (acetonitrile) provided the title compound as a white crystalline solid (3.23 g, 66 %), 1H NMR (300 MHz, DMSO-J6) delta 2.01-2.06 (9H, d, J= 15.3 Hz, P(CHs)3), 4.01-4.07 (2H, d, J= 16.4 Hz, PCH2CN);31P NMR (121.5 MHz, DMSO-J6) delta 32.9.

The chemical industry reduces the impact on the environment during synthesis 2-Iodoacetonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; STERIX LIMITED; WO2007/68905; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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. 624-75-9.

To a mixture of 5-bromo-2-isopropyl-4-methoxy-phenol from step 4 (0.831 g, 3.4 mmol) and K2CO3 (0.562 g, 4.1 mmol) in 17 mL dimethyl formamide (DMF) was added iodoacetonitrile (0.594 g, 3.6 mmol). The mixture was warmed to 60 C. for 30 minutes and then allowed to cool to room temperature. After cooling to room temperature the mixture was taken up in 50 mL of H2O and extracted with 1:1 toluene/ethyl acetate, washed with H2O and then with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo to give a crude solid. Purification via flash chromatography (1:1 hexane/CH2Cl2) afforded (5-bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (0.611 g, 63%) as a while solid.

The synthetic route of 2-Iodoacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2007/49609; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 624-75-9, name is 2-Iodoacetonitrile, 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 624-75-9, 624-75-9

Example 41 Benzyl {(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}(cyanomethyl)carbamate Potassium carbonate (15.7 mg, 113 mmol, 2.1 eq.), 18-crown-6 (30 mg, 113 mmol, 2.1 eq.) and iodoacetonitrile (19 mg, 113 mmol, 2.1 eq.) were added to a solution of benzyl {(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}carbamate (30 mg, 54 mmol) in DMF (2 ml). The reaction mixture was stirred at RT for 12 h and then concentrated under reduced pressure. The residue was acidified with acetic acid and then purified by preparative HPLC (Kromasil C18 column, 5 mum, 50*20 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (25 mg, 78% of theory). LC-MS (Method 5): Rt=1.40 min; MS (ESIpos): m/z (%)=434.0 (100), 550.9 (20), 595.0 (30) [M+H]+; MS (ESIneg): m/z (%)=593.8 (100) [M-H]-. 1H-NMR (400 MHz, DMSO-d6): delta=2.00 (s, 3H), 4.55 (d, 2H), 5.10 (d, 2H), 6.55 (s, 1H), 7.15-7.35 (m, 5H), 7.70-7.95 (m, 7H), 8.15 (br. s, 1H).

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, 2-Iodoacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2012/4203; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

624-75-9,Some common heterocyclic compound, 624-75-9, name is 2-Iodoacetonitrile, molecular formula is C2H2IN, 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: Individual solutions of secondary N-alpha-trimethylsilylmethyl-N-benzylamines19 (5mmol) in acetonitrile (100mL) containing K2CO3 (10mmol) and 2-iodoacetonitrile (4.5mmol) were stirred for 12hat room temperature and concentrated in vacuo to give residues that were partitioned between water and CH2Cl2. The CH2Cl2 layers were dried and concentrated in vacuo to afford residues that were subjected to silica gel column chromatography (EtOAc/hexane=1: 15 – 1: 30) to yield corresponding alpha-aminonitiriles 11a18 (91%), 11b (74%), 11c (78%), 11d (85%), 11e (75%), 11f (75%), 11g (74%), 11h (75%), 11i (78%), 11j (78%) and 11k (66%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Iodoacetonitrile, its application will become more common.

Reference:
Article; Lim, Suk Hyun; Cho, Dae Won; Choi, Jungkweon; An, Hyunjun; Shim, Jun Ho; Mariano, Patrick S.; Tetrahedron; vol. 73; 44; (2017); p. 6249 – 6261;,
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. 624-75-9 name is 2-Iodoacetonitrile, 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. 624-75-9

A 500-mL three-neck round-bottomed flask equipped with an addition funnel, thermometer and charged with 120a (6.70 g, 37.4 mmol), iodoacetonitrile (12.5 g, 74.9 mmol), iron (II) sulfate heptahydrate (5.20 g, 18.7 mmol) and dimethyl sulfoxide (250 mL). Hydrogen peroxide (35%, 18.2 g, 187 mmol) was added dropwise to the mixture over the period of 1 h through a syringe pump at room temperature using a water bath. Iron (II) sulfate heptahydrate (2 to 3 equivalent) was added to the reaction mixture in portions to keep the temperature between 25 C. to 35 C., until the color of the reaction mixture was deep red. When TLCs showed the reaction was not complete, more hydrogen peroxide (2-3 equivalent) and more iron (II) sulfate heptahydrate (1-2 equivalents) were added in the same manner until the reaction was complete. After that time, the reaction mixture was partitioned between saturated sodium bicarbonate solution (200 mL) and ethyl acetate (400 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (2*100 mL). The combined organic layers were washed with saturated sodium thiosulfate solution (50 mL), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to afford a 78% yield (6.40 g) of 120b as a yellow oil: 1H NMR (500 MHz, CDCl3) delta 6.23 (s, 1H), 4.23 (s, 2H), 3.94 (t, 2H, J=6.5 Hz), 3.81 (s, 3H), 2.74 (t, 2H, J=6.5 Hz), 2.00 (m, 2H), 1.83 (m, 2H); (APCI+) m/z 219.3 (M+H)

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

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Young, Wendy B.; US2013/116262; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com