Ammonia → 1H-benzimidazole-2-carbonitrile

HRID 1608696Notes

Reaction equation

HRID 1608696 reaction equation
Cl[C:2](Cl)(Cl)[C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH3:14].Cl.C(OCC)(=O)C>C(O)C>[C:2]([C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:14]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 77133Benzimidazole, 2-trichloromethyl-2×

Product 1

HCID 8438581H-benzimidazole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.2 Grams of a 2-(trichloromethyl)benzimidazole compound [compound (101)] of the formula (XI) in which X is H and Z is OCF2CFHO was dissolved in 30 ml of ethanol. The resulting solution was added by drops to 4 ml of a 25% aqueous ammonia at 5° C. After stirring for 1 hour at 5° to 15° C., the reaction solution was poured into an ice/conc. hydrochloric acid mixture and extrac.ted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. Removing the solvent from the dried layer by distillation gave 2.83 g of a 2-cyanobenzimidazole compound [compound (i)] of the formula (II) in which X is H and Z is OCF2CFHO.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customRemoving the solvent from the dried layer
  4. distillationby distillation

Sources & evidence

ORD record
ord-2c9fa60da1bd4789b427a14a2d267ffd
Source dataset
uspto-grants-1995_03
Patent number
US05395952

Reaction notes

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