Hydrochloric Acid → Ethyl 5-cyano-2-(2,6-dichloro-4-trifluoromethyl-phenyl)-imidazole-4-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]1[NH:14][C:15]([C:20]#N)=[C:16]([C:18]#[N:19])[N:17]=1.[CH2:22]([OH:24])[CH3:23].Cl.[OH2:26]>>[C:18]([C:16]1[NH:17][C:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:5][C:4]=2[Cl:12])=[N:14][C:15]=1[C:20]([O:24][CH2:22][CH3:23])=[O:26])#[N:19]Participants
Procedure
A mixture of 2-(2,6-dichloro-4-trifluoromethylphenyl)-4,5-dicyanoimidazole (3.3 g, 0.01 mol), ethanol (10 ) and concentrated hydrochloric acid (10 ml) was stirred and heated at reflux for 24 hours. After cooling the mixture was poured into water (50 ml) and extracted with dichloromethane (2×50 ml). The combined extracts were washed with water (50 ml), dried over anhydrous sodium sulphate and evaporated to dryness. The residue was purified by mplc on silica eluted with a mixture of ethyl acetate and petroleum spirit (b.p. 60°-80° C.) (1:1) to give ethyl 5-cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)-imidazole-4-carboxylate (0.35 g) m.p. 180°-181° C., after recrystallisation from a mixture of toluene and petroleum spirit (b.p. 60°-80° C.) (1:2), as a white solid.
Workup
- temperatureheated
- temperatureat reflux for 24 hours
- temperatureAfter cooling the mixture
- extractionextracted with dichloromethane (2×50 ml)
- washThe combined extracts were washed with water (50 ml)
- dry with materialdried over anhydrous sodium sulphate
- customevaporated to dryness
- customThe residue was purified by mplc on silica
- washeluted with a mixture of ethyl acetate and petroleum spirit (b.p. 60°-80° C.) (1:1)
Sources & evidence
- ORD record
- ord-243c9a0294cc40ccb996c22831979d01
- Source dataset
- uspto-grants-1993_04
- Patent number
- US05206257
Reaction notes
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