Hydrochloric Acid → 1-Methyl-2-(thiophen-2-yl)-1H-imidazole

Participants

Reaction Conditions

Reaction Steps

Methylaminoacetaldehyde dimethyl acetal (0.50 ml, 3.9 mmol), thiophene-2-carbonitrile (0.36 ml, 3.9 mmol) and copper(I) chloride (481 mg, 4.86 mmol) were combined in a sealed tube and heated to 85° C. for 12 hours. The mixture was allowed to reach ambient temperature, and methanol (2 ml) was added, followed with hydrochloric acid (4.8 M, 2.0 ml, 9.7 mmol). The resulting mixture was refluxed for 4 hours and concentrated under reduced pressure to remove methanol. The mixture was placed over an ice bath and 50% aqueous sodium hydroxide (1.24 g, 31.1 mmol) was added slowly to keep the temperature below 20° C. Then the mixture was diluted with ethyl acetate, stirred for 5 mins, filtered and washed with ethyl acetate. The filtrate was washed with brine, separated, dried over sodium sulfate, filtered and concentrated and taken forward without additional purification. LRMS (ESI) calculated for C8H9N2S [M+H]+, 165.0; found 165.1.

Provenance & Evidence