Imidazole → Benzonitrile, p-imidazol-1-yl-
Reaction equation
CN(C)C=O.F[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1.[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1.[H-].[Na+]>O>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:8][CH:9]=1)#[N:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
1500 ml of dry dimethylformamide (DMF) are placed in a 1000 ml four-necked flask while passing nitrogen over it and 72.67 g (0.6 mol) of 4-fluorocyanobenzene and 61.2 g (0.9 mol) of imidazole and finally 21.6 g (0.9 mol) of sodium hydride are added. The reaction mixture is heated to 100° C., stirred at this temperature for 4 hours and subsequently overnight at room temperature. The reaction mixture is then poured into water and the resulting mixture is extracted a number of times with dichloromethane. The organic phase is dried, evaporated on a rotary evaporator and finally dried further at 60° C. under reduced pressure. The yield is 94 g (93% of theory).
Workup
- additionare added
- extractionthe resulting mixture is extracted a number of times with dichloromethane
- customThe organic phase is dried
- customevaporated on a rotary evaporator
- customfinally dried further at 60° C. under reduced pressure
Sources & evidence
- ORD record
- ord-012ade525109479aa064c2cc28e46630
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877937B2
Reaction notes
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