Acetyl chloride → HCID 20070873, compound

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.46 g, 4.4 mmol) was added dropwise to a stirred suspension of 3-(aminomethyl)thiophene hydrochloride (0.6 g, 4 mmol) in dry dichloromethane (20 ml) maintained under nitrogen at -5° C. After 15 minutes acetyl chloride (0.31 g, 4 mmol) was added dropwise to the solution which was then stirred for 3 hours at -5° C. After this time the reaction mixture was washed sequentially with dilute HCl (50 ml, 0.5M) and dilute NaOH (50 ml, 0.5 m). The organic layer was separated, dried with magnesium sulphate, and the solvent removed in vacuo to yield the crude product which was recrystallised from hexane to give N-(3-thienylmethyl)acetamide (0.52 g, 85%) M.p. 46°-47° C. (Found: C, 53.5; H, 6.2; N. 8.7, S, 20.4. Calculated for C7H9NOS: C, 54.2; H, 5.8, N, 9.0; S, 20.7 (%); IR (Nujol): 3250, 1650 cm-1 ; EI m/e Intensity (%): 155 (37, M+), 112 (55, C4H3S.CH2NH+), 97 (29, C4H3S.CH2+). 83 (12, C4H3S); δH(CDCl3) 7.00-7.29 (3H, m), 6.26 (1H, br,s), 4.41 (2H, d), 1.93 (3H, s); δC(CDCl3): 23.1, 38.7, 122.2, 126.3, 127.3, 139.8, 170.0 ppm.

Provenance & Evidence