Butanal → 7-[Butyl(4-methoxyphenyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.100 g (0.37 mmol) of 7-[(4-methoxyphenyl)amino]-1-methyl-1,3-dihydro-2H-benzimidazol-2-one and 0.13 mL (1.5 mmol) of butyraldehyde in 15 mL of dichloroethane was treated with four drops of glacial acetic acid and 0.31 g (1.5 mmol) of sodium triacetoxyborohydride. The mixture was heated to 70° C. for five days. The mixture was diluted with ethyl acetate and was washed successively with saturated sodium bicarbonate and brine before being dried over sodium sulfate. The solution was filtered, concentrated in vacuo and the resulting crude oil was purified by flash chromatography eluting with a 97% dichloromethane/methanol mixture to give 0.70 g (45%) of the title compound as a yellow sticky semi-solid that was used without further purification.

Provenance & Evidence