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

HRID 904830ノート

反応式

HRID 904830 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-3eb1a86485fc4bccb5870f8ec1ad44fd
出典データセット
uspto-grants-1983_12
特許番号
US04420479

反応ノート

読み込み中…