O-Phenylenediamine → Benzimidazole, 2-trichloromethyl-

HRID 1608699Notes

Reaction equation

HRID 1608699 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

2.5 Grams of an o-phenylenediamine compound [compound (201)] of the formula (XII) in which X is H and Z is OCF2CFHO was dissolved in 50 ml of acetic acid. 3.8 Grams of methyl trichloroacetoimidate was added thereto at room temperature. The resulting mixture was stirred for 1 hour. 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 3.2 g of a 2-(trichloromethyl)benzimidazole compound [compound (101)] of the formula (XI) in which X is H and Z is OCF2CFHO.

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 from the dried layer
  8. distillationby distillation

Sources & evidence

ORD record
ord-8ac944f873e54b1895625320f2dbee64
Source dataset
uspto-grants-1995_03
Patent number
US05395952

Reaction notes

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