Dimethylamine → HCID 15007350, compound

Participants

Reaction Steps

To a solution of 5-formyl-2-thiophenecarboxylic acid (prepared according to Carpenter, A. J., et al., Tetrahedron 41:3808 (1985)) (2.75 g. 17.61 mmoles) in 75 ml of tetrahydrofuran was added 1,1'-carbonyldiimidazole (3.71 g, 22.88 mmoles), the solution stirred under dry argon for 21/2 hours and treated with excess gaseous dimethylamine. The solution was concentrated in vacuo to an oil which was dissolved in ethyl acetate (100 ml) and extracted with 1N hydrochloric acid (2×50 ml) followed by 5% sodium bicarbonate (2×50 ml). Each of the aqueous layers was backwashed with ethyl acetate (2×50 ml) and the combined organic layers were dried (magnesium sulfate). Concentration in vacuo furnished a pale yellow solid (2.42 g, 75%). EIMS (m/z): 183 (M+, 82%), 154 (M+ -CHO, 7%), 139 (M+ -(CH3)2N, base) and 111 (M+ -(CH3)2NCO, 59%; 1HNMR (CDCl3) delta, 9.91 (1H, s), 7.67 (1H, d, J=4.0Hz), 7.35 (1H, d, J=4.0Hz), 3.13 (6H, br s). This material was used directly without further purification.

Provenance & Evidence