p-Toluenesulfonic acid → 1-Isopropylsulfonyl-2-amino-6-(alpha-aminocarbonylmethylenebenzyl)benzimidazole

HRID 904830노트

반응식

HRID 904830 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:12]([S:15]([N:18]1[C:22]2[CH:23]=[C:24]([C:27](O)([CH2:34][C:35]([NH2:37])=[O:36])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[NH2:39])(=[O:17])=[O:16])([CH3:14])[CH3:13]>C(Cl)(Cl)Cl>[CH:12]([S:15]([N:18]1[C:22]2[CH:23]=[C:24]([C:27](=[CH:34][C:35]([NH2:37])=[O:36])[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:25]=[CH:26][C:21]=2[N:20]=[C:19]1[NH2:39])(=[O:16])=[O:17])([CH3:14])[CH3:13]

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 204777191-Isopropylsulfonyl-2-amino-6-(alpha-hydroxy-alpha-aminocarbonylmethylbenzyl)benzimidazole

생성물 1

HCID 47132911-Isopropylsulfonyl-2-amino-6-(alpha-aminocarbonylmethylenebenzyl)benzimidazole수율 35%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A solution of 3.0 g. of p-toluenesulfonic acid and 3.0 g. of 1-isopropylsulfonyl-2-amino-6-(α-hydroxy-α-aminocarbonylmethylbenzyl)benzimidazole (prepared as described in Example 23) in 100 ml. of chloroform was heated at reflux for four hours. The reaction mixture then was cooled, washed with aqueous sodium bicarbonate solution and with water, dried, and the solvent was removed by evaporation under reduced pressure. Crystallization of the product thus formed from tetrahydrofuran afforded 1.1 g. of trans-1-isopropylsulfonyl-2-amino-6-(α-aminocarbonylmethylenebenzyl)benzimidazole, M.P. 218°-219° C. Yield 35%, and 1.0 g. of the corresponding cis-isomer, M.P. 211°-212° C., yield 32%.

후처리

  1. temperatureat reflux for four hours
  2. temperatureThe reaction mixture then was cooled
  3. washwashed with aqueous sodium bicarbonate solution and with water
  4. customdried
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customCrystallization of the product
  7. customthus formed from tetrahydrofuran
  8. customafforded 1.1 g

출처 및 근거

ORD 기록
ord-3eb1a86485fc4bccb5870f8ec1ad44fd
출처 데이터셋
uspto-grants-1983_12
특허 번호
US04420479

반응 노트

불러오는 중…