2-Fluorobenzoyl chloride → 2-(2-fluorobenzoyl)-N-methyl-1-hydrazinecarbothioamide

Reaction equation

[CH3:1][NH:2][C:3](=[S:6])[NH:4][NH2:5].[F:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](Cl)=[O:11].Cl.N1C=CC=CC=1>N1C=CC=CC=1>[F:7][C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH:5][NH:4][C:3]([NH:2][CH3:1])=[S:6])=[O:11]

Participants

Procedure

To a stirred room temperature solution of 4-methylthiosemicarbazide (10.5 g, 1.00×10-1 mole) and pyridine (250 ml), 2-fluorobenzoyl chloride (11.9 ml, 1.00×10-1 mole) was added dropwise. After stirring overnight at room temperature the excess pyridine was evaporated at reduced pressure first on a rotary evaporator and then at high vacuum. This afforded a mixture of the desired product and pyridine hydrochloride which is used without further purification in the subsequent cyclization step.