Ammonia → 1H-benzimidazole-2-carbonitrile

HRID 1033222Notes

Reaction equation

HRID 1033222 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]>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

4

Reactant 2

HCID 222AmmoniaHCID 77133Benzimidazole, 2-trichloromethyl-2×

Product 1

HCID 8438581H-benzimidazole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.3 Grams of 2-(trichloromethyl)benzimidazole compound [compound (104)] of the formula (XI) in which X is H and Z is OCF2O was suspended in 100 ml of ethanol. The resulting solution was added by drops to 40 ml of a 25% aqueous ammonia at 5° C. After stirring for 1 hour at 5° C. to room temperature, the reaction solution was poured into an ice/conc. hydrochloric acid mixture and extracted 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 4.0 g of a 2-cyanobenzimidazole compound [compound (iv)] of the formula (II) in which X is H and Z is OCF2O.

Workup

  1. extractionhydrochloric acid mixture and extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customRemoving the solvent from the dried layer
  5. distillationby distillation

Sources & evidence

ORD record
ord-c2c55a029aa84f47aee5eac07f8ae2a0
Source dataset
uspto-grants-1994_05
Patent number
US05310747

Reaction notes

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