Methyl 2-chloroacrylate → 5-Chloro-5-methoxycarbonyl-3-thiapentanamide

Reaction equation

[SH:1][CH2:2][C:3]([NH2:5])=[O:4].[Cl:6][C:7](=[CH2:12])[C:8]([O:10][CH3:11])=[O:9].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:6][CH:7]([C:8]([O:10][CH3:11])=[O:9])[CH2:12][S:1][CH2:2][C:3]([NH2:5])=[O:4]

Participants

Procedure

2-Mercaptoacetamide (10.0 g) and methyl 2-chloroacrylate (13.24 g) were dissolved in warm acetone (100 ml), and potassium carbonate (7.58 g) was added in one portion. Heat was evolved. The mixture was heated to reflux for 2 hours. The red solution was filtered hot using a filter aid, and the residue washed with hot acetone (×2). The filtrate and washings were combined and evaporated to obtain the title compound as a red oil (19.92 g) 1H n.m.r. δ (CDCl3 /DMSO-d6) 3.05-3.18 (4H, overlapping s and d, CH2COR and CH2CH) 3.76 (3H,s,CO2Me), 4.67 (1H,t, J=7Hz, CHCH2), 6.92 (1H, br s, CONH), 7.43 (1H, br s, CONH).