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

HRID 904830Notes

Reaction equation

HRID 904830 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-3eb1a86485fc4bccb5870f8ec1ad44fd
Source dataset
uspto-grants-1983_12
Patent number
US04420479

Reaction notes

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