Methyl iodide → HCID 178503951, compound

Reaction equation

[CH3:1][C:2]([CH3:15])=[CH:3][C:4]([NH:6][C:7]([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[S:8])=[O:5].[C:16](=O)([O-])[O-].[Na+].[Na+].IC>O1CCCC1>[CH3:16][S:8]/[C:7](=[N:6]\[C:4](=[O:5])[CH:3]=[C:2]([CH3:15])[CH3:1])/[N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

Procedure

A mixture of 3-methyl-N-(piperidine-1-carbonothioyl)but-2-enamide (3.21 g, 14.2 mmol, Eq: 1.00), sodium carbonate (1.58 g, 14.9 mmol, Eq: 1.05) and iodomethane (10.1 g, 4.43 ml, 70.9 mmol, Eq: 5) in tetrahydrofuran (100 ml) was stirred for 2.5 days under reflux. The mixture was evaporated, 30 ml of ethyl acetate was added and the mixture was filtrated, the filtrate was evaporated affording 3-methyl-but-2-enoic acid 1-methylsulfanyl-1-piperidin-1-yl-meth-(Z)-ylideneamide (5.137 g, 151%) as an orange-brown semi-solid. MS: m/z=241.2 (M+H+)