O-Phenylenediamine → Benzimidazole, 2-trichloromethyl-

HRID 1608700Notes

Reaction equation

HRID 1608700 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[Cl:9][C:10]([Cl:16])([Cl:15])[C:11](=N)OC>C(O)(=O)C>[Cl:9][C:10]([Cl:16])([Cl:15])[C:11]1[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[N:8]=1

Participants

4

Reactant 2

HCID 7243O-Phenylenediamine2×HCID 100479Methyl 2,2,2-trichloroacetimidate

Product 1

HCID 77133Benzimidazole, 2-trichloromethyl-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.6 Grams of an o-phenylenediamine compound [compound (204)] of the formula (XII) in which X is H and Z is OCF2O was dissolved in 80 ml of acetic acid. 8.7 Grams of methyl trichloroacetoimidate was added thereto at room temperature. The resulting mixture was stirred for 20 minutes. The reaction solution was poured into ice water, and precipitated crystals were filtered off. The crystals were dissolved in ethyl acetate. The resulting solution was washed with water and dried over anhydrous sodium sulfate. Removing the solvent from the dried layer.by distillation gave 5.35 g of a 2-(trichloromethyl)benzimidazole compound [compound (104)] of the formula (XI) in which X is H and Z is OCF2O.

Workup

  1. customat room temperature
  2. customprecipitated crystals
  3. filtrationwere filtered off
  4. dissolutionThe crystals were dissolved in ethyl acetate
  5. washThe resulting solution was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customRemoving the solvent
  8. distillationfrom the dried layer.by distillation

Sources & evidence

ORD record
ord-f95606c990d5447aae3413292d6a4b6c
Source dataset
uspto-grants-1995_03
Patent number
US05395952

Reaction notes

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