Category: 13918-92-8

Electric Literature of 13918-92-8, A common heterocyclic compound, 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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: Compound 11a (800 mg,2.0 mmol) was dissolved in 10 ml ethyl acetate and then 9 N HCl(5 ml) was added, the reaction mixture was stirred for 30 min at roomtemperature, the reaction solvent was neutralized by NaHCO3 topH=8, 50 ml ethyl acetate and 30 ml H2O was added, after stirredadequately, the organic layer was separated, and concentrated, andthen the crude product was purified by silica gel columnchromatography using a mixture solvent of dichloromethane:methanol (20:1), to give white powder (540 mg); Above whitepowder (150 mg, 0.5 mmol) was dissolved in THF (10 ml),iodomethane (107 mg, 0.75 mmol) and triethylamine (0.5 ml) wereadded in the solvent. After the reaction mixture was stirred for 1 h at room temperature, the solvent was concentrated, the residues was purified by silica gel column chromatography using a mixture solvent ofdichloromethane: methanol (40:1), to give (12aa) Yield 49%, White powder.

The synthetic route of 13918-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Min; Jiang, Li; Tao, Jia; Pan, Zhaoping; He, Mingyao; Su, Dongyuan; He, Gu; Jiang, Qinglin; Bioorganic and Medicinal Chemistry; vol. 27; 11; (2019); p. 2268 – 2279;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13918-92-8, 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. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution of 5-bromo-2-methoxypyridin-3-amine 1 (13.70 g, 67.5 mmol) in pyridine (140 mL) was added dropwise 2,4-difluorobenzenesulfonyl chloride 2 (14.35 g, 67.5 mmol) over 10 min at 0 C. The mixture, which quickly became heterogeneous, was allowed to warm to ambient temperature and stirred for 16 h, at which time the reaction was diluted with water (400 mL) and the solids were filtered and washed with water. The precipitate was dried in a vacuum oven at 60 C to give N-(5-bromo-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide 3 (18.30 g, 71.3% yield) as a pale yellow powder, which was used without further purification. 1H NMR (300 MHz, CDCl3) delta 7.96-7.86 (m, 2H), 7.83 (d, J = 2.2 Hz, 1H), 7.04-6.91 (m, 2H), 3.91 (s, 3H). MS (ESI, positive ion) m/z: 379.17 (M + H+, 79Br), 381.45 (M + H+, 81Br).

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Reference:
Article; Han, Jinsong; Chen, Ying; Yang, Chao; Liu, Ting; Wang, Mingping; Xu, Haojie; Zhang, Ling; Zheng, Canhui; Song, Yunlong; Zhu, Ju; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 684 – 701;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, belongs to chlorides-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 13918-92-8, 13918-92-8

Intermediate 36lambda/-[5-Bromo-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide To a cooled (0 0C) solution of 5-bromo-2-(methyloxy)-3-pyridinamine (13.7 g, 67.5 mmol) in pyridine (200 ml) was added slowly 2,4-difluorobenzenesulfonyl chloride (14.37 g, 67.6 mmol) over 15 min (reaction became heterogeneous). The ice bath was removed and the reaction was stirred at ambient temperature for 16 h. Most of the pyridine was removed in vacuo and the residue diluted with water (500 ml). The solids were filtered off and washed with copious amounts of water to give 21 g of crude desired product. More solid appeared in the mother liquor and was filtered and washed with water to give an additional 1.5 g of desired material. The two batches were combined, triturated with DCM (70 ml) and dried in a vacuum oven at 50 0C to give the title compound (15 g). LCMS (Method B) R1 = 1.11 min, MH+ = 378/380.

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, 2,4-Difluorobenzene-1-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147187; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, I believe this compound will play a more active role in future production and life. 13918-92-8

To 5-bromo-2-methoxy pyridine-3-amine (6.3g, 31mmol) pyridine (25 ml) is added to solution of 2,4-difluoro-1-sulfonyl chloride (16.47g, 77 . 5mmol). Reaction liquid in 23 C stirring 24 hours, concentrated under reduced pressure, the volume of the solution to the original 1/2. Filtering, collecting solid, solid with i-PrOH (5mLx2) and Et 2 O (5 ml) washing. The resulting solid and NaOH (2.48g, 62mmol) suspended in MeOH (25 ml) in, the reaction solution 23 C stirring 1 hour, concentrated under reduced pressure. For residual DCM (20 ml) and 2M hydrochloric acid (20 ml) is diluted, by 5% NaHCO 3 pH7 aqueous solution is adjusted to the rear, with DCM (20mLx3) extraction. Merger of the first organic phase and the salt water (20 ml) washing, anhydrous Na 2 SO 4 drying, and concentrating under reduced pressure, to obtain the title compound as a buff solid (8.2g, 69.9%).

The chemical industry reduces the impact on the environment during synthesis 13918-92-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd. / Sunshine Lake Pharma Co., Ltd; Jiata Science company; Xi, Ning; Li, Zhuo; Wang, Tingjin; Wu, Zuping; Wen, Qiuling; (65 pag.)CN103539777; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, belongs to chlorides-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. 13918-92-8

General procedure: Compound 11a (800 mg,2.0 mmol) was dissolved in 10 ml ethyl acetate and then 9 N HCl(5 ml) was added, the reaction mixture was stirred for 30 min at roomtemperature, the reaction solvent was neutralized by NaHCO3 topH=8, 50 ml ethyl acetate and 30 ml H2O was added, after stirredadequately, the organic layer was separated, and concentrated, andthen the crude product was purified by silica gel columnchromatography using a mixture solvent of dichloromethane:methanol (20:1), to give white powder (540 mg); Above whitepowder (150 mg, 0.5 mmol) was dissolved in THF (10 ml),iodomethane (107 mg, 0.75 mmol) and triethylamine (0.5 ml) wereadded in the solvent. After the reaction mixture was stirred for 1 h at room temperature, the solvent was concentrated, the residues was purified by silica gel column chromatography using a mixture solvent ofdichloromethane: methanol (40:1), to give (12aa) Yield 49%, White powder.

Statistics shows that 13918-92-8 is playing an increasingly important role. we look forward to future research findings about 2,4-Difluorobenzene-1-sulfonyl chloride.

Reference:
Article; Zhang, Min; Jiang, Li; Tao, Jia; Pan, Zhaoping; He, Mingyao; Su, Dongyuan; He, Gu; Jiang, Qinglin; Bioorganic and Medicinal Chemistry; vol. 27; 11; (2019); p. 2268 – 2279;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13918-92-8, Name is 2,4-Difluorobenzene-1-sulfonyl chloride, 13918-92-8, belongs to chlorides-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.

Step EN-(5-bromo-2-meth enzene- sulfonamide[00299] 2,4-difluorobenzene-1-sulfonyl chloride (6.8 g, 32 mmol) was added into a solution of 5-bromo-2-methoxypyridin-3-amine (6.5 g, 32 mmol) in pyridine (10 mL) and the reaction mixture was stirred at r.t. for 20 hours before the reaction solution was concentrated to dry in vacuo to give a crude product which was purified with column chromatography (EtOAc : Petroleum ether = 1 :2 as eluent) to give the product as a brown solid (10 g, 83%). 1 H-NMR (300 MHz, DMSO-d6), delta 10.46 (s, 1 H), 8.52 (s, 1 H), 7.80-7.72 (m, 2H), 7.56 (m, 1 H), 7.20 (m, 1 H), 3.62 (s, 3H). LC/MS, ESI, m/z, 379, 381 (m+1 )+, Br pattern found.

Statistics shows that 2,4-Difluorobenzene-1-sulfonyl chloride is playing an increasingly important role. we look forward to future research findings about 13918-92-8.

Reference:
Patent; GLAXOSMITHKLINE LLC; BOTYANSZKI, Janos; DICKERSON, Scott Howard; LEIVERS, Martin Robert; LI, Xiaofei; MCFADYEN, Robert Blount; REDMAN, Aniko Maria; SHOTWELL, John Bradford; XUE, Jianjun; WO2012/174312; (2012); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, I believe this compound will play a more active role in future production and life. 13918-92-8

General procedure: To a solution of 76 (120 mg, 0.37 mmol) in dry pyridine (12 mL) under N2 at RT, was added 2,4-difluorobenzenesulphonyl chloride (159 mg, 0.74 mmol) in CH2Cl2 (1.5 mL) dropwise over 5 min. The mixture was stirred at 45 C under N2 for 16 , and the solvent then removed under reduced pressure. The reaction was quenched with a little water and the resulting solid collected by filtration and washed with water and Et2O. Purification was carried out by trituration with hot CH2Cl2/MeOH solution to give 4 as a pale brown solid (65%).

The chemical industry reduces the impact on the environment during synthesis 13918-92-8. I believe this compound will play a more active role in future production and life.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; European Journal of Medicinal Chemistry; vol. 137; (2017); p. 139 – 155;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics