p-Toluenesulfonic acid → HCID 54501125, compound

HRID 904823Notes

Reaction equation

HRID 904823 reaction equation
[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16](O)([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:29])(=[O:6])=[O:5])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH:1]([S:4]([N:7]1[C:11]2[CH:12]=[C:13]([C:16](=[CH:23][C:24]([O:26][CH3:27])=[O:25])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH2:29])(=[O:5])=[O:6])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 132864971-Isopropylsulfonyl-2-amino-6-(alpha-hydroxy-alpha-methoxycarbonylmethylbenzyl)benzimidazole

Product 1

HCID 54501125HCID 54501125, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 6.0 g. of 1-isopropylsulfonyl-2-amino-6-(α-hydroxy-α-methoxycarbonylmethylbenzyl)benzimidazole (from Example 4) and 6.0 g. of p-toluenesulfonic acid in 150 ml. of chloroform was heated at reflux for three hours. The solution was cooled to room temperature and washed two times with saturated aqueous sodium bicarbonate solution, and two times with water. After drying the solution over sodium sulfate, the solvent was removed by evaporation under reduced pressure to provide 5.5 g. (96% yield) of 1-isopropylsulfonyl-2-amino-6-(α-methoxycarbonylmethylenebenzyl)benzimidazole. M.P. 160°-165° C.

Workup

  1. temperatureat reflux for three hours
  2. washwashed two times with saturated aqueous sodium bicarbonate solution, and two times with water
  3. dry with materialAfter drying the solution over sodium sulfate
  4. customthe solvent was removed by evaporation under reduced pressure
  5. customto provide 5.5 g

Sources & evidence

ORD record
ord-9bd714e4559943ccaab3c2ad4ebc3d47
Source dataset
uspto-grants-1983_12
Patent number
US04420479

Reaction notes

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