O-Phenylenediamine → Benzimidazole, 2-trichloromethyl-

HRID 2254109Notes

Reaction equation

HRID 2254109 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:16])[C:5]([NH2:15])=[CH:6][C:7]=1OC(F)(F)C(F)F.C1(N)C=CC=CC=1N.BrBr.[Cl:27][C:28]([Cl:34])([Cl:33])[C:29](=N)OC>C(O)(=O)C>[Cl:27][C:28]([Cl:34])([Cl:33])[C:29]1[NH:16][C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][C:5]=2[N:15]=1

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 24408BromineHCID 100479Methyl 2,2,2-trichloroacetimidateHCID 19744233HCID 19744233, compound

Product 1

HCID 77133Benzimidazole, 2-trichloromethyl-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9.5 Grams of 4-bromo-5-(1',1',2',2'-tetrafluoroethoxy)-1,2-benzenediamine, [i.e. the o-phenylenediamine compound (IV) containing bromine as the substituent X] was dissolved in 100 ml of acetic acid, 5.7 ml of methyl trichloroacetoimidate was added thereto at room temperature, and the resulting mixture was stirred for 20 minutes. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and recrystallized from hexane-ethyl acetate to obtain 5.0 g of 5(6)-bromo-6(5)-(1',1',2',2'-tetrafluoroethoxy)-2-tetrafluoroethoxy)-2-(trichloromethyl)-benzimidazole. 1H-NMR (CDC3 3+DMSO-d6): δ(ppm) (1H, s), 7.45(1H), 5.97(1H, tt, 7.77 (1H, s), 7.45(1H), 5.97 (1H, tt, J=3, 53 Hz)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-26b10f46a299420687151a71a50a9b0d
Source dataset
uspto-grants-1993_08
Patent number
US05234938

Reaction notes

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