Acetyl chloride → HCID 20070873, compound

HRID 981780Notes

Reaction equation

C(N(CC)CC)C.Cl.[NH2:9][CH2:10][C:11]1[CH:15]=[CH:14][S:13][CH:12]=1.[C:16](Cl)(=[O:18])[CH3:17]>ClCCl>[S:13]1[CH:14]=[CH:15][C:11]([CH2:10][NH:9][C:16](=[O:18])[CH3:17])=[CH:12]1

Participants

Conditions

Temperature: -5 °C

Procedure

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.

Workup

washAfter this time the reaction mixture was washed sequentially with dilute HCl (50 ml, 0.5M) and dilute NaOH (50 ml, 0.5 m)
customThe organic layer was separated
dry with materialdried with magnesium sulphate
customthe solvent removed in vacuo
customto yield the crude product which
customwas recrystallised from hexane

Sources & evidence

ORD record: ord-ed5d4f80b8f743b29a15c847215d5db4
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04992559

Reaction notes

Loading…