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 ml) 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 of 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-trifluoromethyl-phenyl)-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 of silica
- washeluted with a mixture of ethyl acetate and petroleum spirit (b.p. 60°-80° C.) (1:1)
Sources & evidence
- ORD record
- ord-9df3d329dc91459ea23e84a73a15912d
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05380865
Reaction notes
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