Dimethylamine → HCID 15007350, compound

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′-carbonyl-diimidazole (3.71 g, 22.88 mmoles), the solution stirred under dry argon for ½ 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=4.0 Hz), 7.35 (1H, d, J=4.0 Hz), 3.13 (6H, br s). This material was used directly without further purification.

1. concentrationThe solution was concentrated in vacuo to an oil which
2. dissolutionwas dissolved in ethyl acetate (100 ml)
3. extractionextracted with 1N hydrochloric acid (2×50 ml)
4. dry with materialthe combined organic layers were dried (magnesium sulfate)
5. concentrationConcentration in vacuo

ORD record

ord-39c2db13038e47858f7a76c8fd4900c4

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06174883B1