Ammonia → 1H-benzimidazole-2-carbonitrile
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
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
1.0 Gram of a 2-(trichloromethyl)benzimidazole compound [compound (107)] of the formula (XI) in which X is H and Z is CF2CF2O was dissolved in 20 ml of ethanol. The resulting solution was added by drops to 5 ml of a 25% aqueous ammonia at 5° C. After stirring for 30 minutes at 5° C. 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 0.6 g of a 2-cyanobenzimidazole compound [compound (vii)] of the formula (II) in which X is H and Z is CF2CF2O.
Workup
- extractionhydrochloric acid mixture and extracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customRemoving the solvent from the dried layer
- distillationby distillation
Sources & evidence
- ORD record
- ord-b8404a948ecb4b21aafa2b29fc6a7242
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05395952
Reaction notes
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