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A kind of method preparing 2-aminoethylsulfonamide hydrochloride

A technology of aminoethylsulfonamide and hydrochloride, applied in the preparation of sulfonic acid amide, organic chemistry and other directions, can solve problems such as complex preparation process, and achieve the effects of simple preparation process, no discharge of three wastes, and high reaction yield

Active Publication Date: 2018-04-13
HENAN CHEM IND RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing synthesis method has: method Preparation of sulfonyl chloride from taurine under the protection of benzyloxycarbonyl, ammonolysis, and catalytic hydrogenation to remove the amino protection group to obtain taurine hydrochloride [Journal of American Chemical Society, 2006, 128, 1995-2004; US2012208833A1]; method Taurine prepares sulfonyl chloride under the protection of phthalic anhydride, ammonolysis, and removes the amino protection group under the action of hydrazine hydrate to obtain taurine hydrochloride [Bioorganic & Medicinal Chemistry Letters, 1998, 8, 1607- l 612; Journal of Medicinal Chemistry, 2010, 53, 2390–2400; EP2077263A1]; but the existing synthesis method will produce a large amount of waste liquids such as acetic acid, tetrahydrofuran, dioxane and phosphorus oxychloride, and the preparation process is complicated

Method used

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  • A kind of method preparing 2-aminoethylsulfonamide hydrochloride
  • A kind of method preparing 2-aminoethylsulfonamide hydrochloride
  • A kind of method preparing 2-aminoethylsulfonamide hydrochloride

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (1) Preparation of intermediate 1

[0021] Add 55.56 g (0.3 mol) of potassium phthalimide and 300 ml of N,N-dimethylformamide into a 500 ml three-necked flask, and add 16.3 chloroethylsulfonyl chloride dropwise at room temperature gram (0.1 mol), the dropping speed kept the reaction temperature not exceeding 60°C, and the dropwise addition was completed within 1 hour; after reacting at room temperature for 30 hours, suction filtered, and vacuum-dried at 60°C for 10 hours to obtain 52.86 grams of white solid intermediate 1 , the yield was 91.77 %; melting point: 239.1-239.7 ℃; IR (KBr pellet, cm −1 ): 2947.2, 2362.8, 2341.5, 1793.8, 1782.2, 1745.5, 1705.1, 1462, 1440.8,1388.7, 1363.6, 1259.5, 1217.1, 1178.5, 1103.2,1035.7, 974, 864.1, 850.6,713.6, 563.2, 516.2, 482.2; 1 H NMR (400 MHz, DMSO-D 6 ) δ(ppm): 7.91-7.80(m, 4H),7.79-7.74(m, 4H), 4.11(s, 4H); HRMS (ESI) m / z 385.0517 (M+H) + .

[0022] (2) Preparation of 2-aminoethylsulfonamide hydrochloride

[0023] 38.4 gr...

Embodiment 2

[0025] (1) Preparation of intermediate 1

[0026] Add 55.56 g (0.3 mol) of potassium phthalimide and 300 ml of N,N-dimethylformamide into a 500 ml three-necked flask, and add 24.45 chloroethylsulfonyl chloride dropwise at room temperature gram (0.15 mol), the rate of addition kept the reaction temperature not exceeding 60°C, and the dropwise addition was completed within 1 hour. After reacting at room temperature for 10 hours, suction filtration, and vacuum drying at 60°C for 10 hours gave 51.59 grams of white solid intermediate 1 , the yield was 89.57 %; melting point: 239.1-239.7 ℃; IR (KBr pellet, cm −1 ): 2947.2, 2362.8, 2341.5, 1793.8, 1782.2, 1745.5, 1705.1, 1462,1440.8, 1388.7, 1363.6, 1259.5, 1217.1, 1178.5, 1103.2,1035.7, 974, 864.1,850.6, 713.6, 563.2, 516.2, 482.2; 1 H NMR (400 MHz, DMSO-D 6 ) δ(ppm): 7.91-7.80(m, 4H), 7.79-7.74(m, 4H), 4.11(s, 4H); HRMS (ESI) m / z 385.0517 (M+H) + .

[0027] (2) Preparation of 2-aminoethylsulfonamide hydrochloride

[0028]38.4 ...

Embodiment 3

[0030] (1) Preparation of intermediate 1

[0031] 55.56 grams (0.3 mol) of potassium phthalimide and 300 milliliters of acetonitrile were added to a 500 milliliter three-necked flask, and 24.45 grams (0.15 mol) of chloroethylsulfonyl chloride were added dropwise at room temperature. Keeping the reaction temperature not exceeding 60°C, the dropwise addition was completed within 1 hour, after reacting at room temperature for 10 hours, suction filtration, and vacuum drying at 60°C for 10 hours to obtain 51.42 grams of white solid intermediate 1 with a yield of 89.27%; melting point : 239.1-239.7 ℃; IR (KBr pellet, cm −1 ):2947.2, 2362.8, 2341.5, 1793.8, 1782.2, 1745.5, 1705.1, 1462, 1440.8, 1388.7,1363.6, 1259.5, 1217.1, 1178.5, 1103.2,1035.7, 974, 864.1, 850.6, 713.6,563.2, 516.2, 482.2; 1 H NMR (400 MHz, DMSO-D 6 ) δ(ppm): 7.91-7.80(m, 4H), 7.79-7.74(m, 4H), 4.11(s, 4H); HRMS (ESI) m / z 385.0517 (M+H) + .

[0032] (2) Preparation of 2-aminoethylsulfonamide hydrochloride

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Abstract

The invention relates to a method for preparing 2-amino ethanesulfonamide hydrochloride. The method comprises the following steps: (1) reacting by virtue of chloroethylsulfonyl chloride with phthalimide potassium salt, so as to prepare N-(2- phthalimide ethyl sulfonyl)phthalimide (intermediate 1); and (2) reacting by virtue of the intermediate 1 with sodium borohydride, so as to prepare 2-aminoethanesulfonamide, and carrying out hydrochloric acid acidification, so as to obtain 2-amino ethanesulfonamide hydrochloride. The method is characterized in that 2-amino ethanesulfonamide hydrochloride is prepared from chloroethylsulfonyl chloride for the first time, a preparation process is simple, and waste liquids such as acetic acid, tetrahydrofuran, dioxane, hydrazine hydrate and phosphorus oxychloride are not produced.

Description

technical field [0001] The invention relates to a method for preparing 2-aminoethylsulfonamide hydrochloride, in particular to a method for preparing N-(2-phthalimidoethanesulfonyl)phthalimide. Background technique [0002] Taurolidine is a broad-spectrum non-antibiotic antibacterial agent with good antibacterial and anti-endotoxin effects. It is widely used clinically in the treatment of peritonitis, otitis, pleural empyema, osteitis, osteomyelitis, and dermatitis , Periodontitis, gingivitis, acne, erythematous acne and various ulcers, prevention of postoperative infection, etc. Studies have shown that the use of taurolidine infusion to treat sepsis, bronchiectasis, and postoperative infection complications has a good effect; in recent years, with the abuse of antibiotics, almost all conventional antibiotics have corresponding drug resistance, Compared with antibiotics, taurolidine does not induce any microbial resistance, has good tolerance and no drug resistance, and has...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/36C07C311/32C07D209/48
CPCC07C303/36C07D209/48C07C311/32
Inventor 霍二福成兰兴赵增兵程伟琴王延花王毅楠冯明王柏楠赵怡丽谷中鸣张谦华邢文听武臻王静侯占峰郝凌云吴泽鑫张晓阁刘菲李迎春陈蔚付政辉郭剑峰王雪洁孟立山张洪峰魏新军黄尚国卢磊王平宁红军田国峰
Owner HENAN CHEM IND RES INST
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