Hydrochloric Acid → 5-Cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)-imidazole-4-carboxamide

HRID 1769287Notes

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:21])=[C:16]([C:18]#[N:19])[N:17]=1.[OH-:22].[Na+].Cl>O>[C:20]([C:15]1[NH:14][C:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][C:4]=2[Cl:12])=[N:17][C:16]=1[C:18]([NH2:19])=[O:22])#[N:21]

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 2-(2,6-dichloro-4-trifluoromethylphenyl)-4,5-dicyanoimidazole (3.31 g, 0.01 mol) and sodium hydroxide (1.0 g, 0,025 mol) in water (10 ml) was stirred and heated at 40° C. overnight. Concentrated hydrochloric acid was added to the mixture and the precipitated solid was filtered off and purified by medium pressure liquid chromatography (mplc) on silica eluted with a mixture of ethyl acetate and dichloromethane (1:1). Recrystallization of the white solid from a mixture of ethyl acetate and petroleum spirit (bp 60°-80° C.) (1:1) gave 5-cyano-2-(2,6-dichloro-4-trifluoromethylphenyl)-imidazole-4-carboxamide (0.61 g), m.p. 254°-255° C., as a white solid.

Workup

filtrationthe precipitated solid was filtered off
custompurified by medium pressure liquid chromatography (mplc) on silica
washeluted with a mixture of ethyl acetate and dichloromethane (1:1)
customRecrystallization of the white solid
additionfrom a mixture of ethyl acetate and petroleum spirit (bp 60°-80° C.) (1:1)

Sources & evidence

ORD record: ord-72c09cd193294b8389300c75c47052d7
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380865

Reaction notes

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