Water → Benzimidazole, 2-trichloromethyl-

HRID 1850248Notes

Reaction equation

HRID 1850248 reaction equation
C(O[C:9](=N)[C:10]([Cl:13])([Cl:12])[Cl:11])C1C=CC=CC=1.[C:15]1([NH2:22])[C:16]([NH2:21])=[CH:17][CH:18]=[CH:19][CH:20]=1.O>C(O)(=O)C>[Cl:11][C:10]([Cl:13])([Cl:12])[C:9]1[NH:22][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7243O-PhenylenediamineHCID 144968Benzyl 2,2,2-trichloroacetimidate

Product 1

HCID 77133Benzimidazole, 2-trichloromethyl-Yield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,2,2-trichloro-acetimidic acid benzyl ester (16) (2.3 g, 9.22 mmol, Alfa Aesar) was added to a solution of Benzene-1,2-diamine (15) (1.0 g, 9.2 mmol) in acetic acid (30 mL), the solution was stirred at RT for 1 h. H2O (20 mL) was added to the mixture and the suspension was filtered. The filter cake was washed with water and dried under vacuum to afford compound (17) (1.90 g yield 88%) which was used directly for the next step without further purification. ESI-MS (M+1): 235 calc. for C8H5Cl3N2 234.

Workup

  1. filtrationthe suspension was filtered
  2. washThe filter cake was washed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-7df555842da24fa88fe95c14cd5079b9
Source dataset
uspto-grants-2015_02
Patent number
US08957073B2

Reaction notes

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