Hydrochloric Acid → 4-Fluorobenzothiohydrazide hydrochloride

Reaction equation

C(OC([NH:8][NH:9][C:10](=[S:18])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O)(C)(C)C.[ClH:19].O1CCOCC1>>[ClH:19].[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][NH2:8])=[S:18])=[CH:12][CH:13]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 866375961,1-Dimethylethyl 2-[(4-fluorophenyl)thioxomethyl]hydrazinecarboxylate

Product 1

HCID 866375974-Fluorobenzothiohydrazide hydrochloride

Procedure

To N′-(4-fluoro-thiobenzoyl)-hydrazinecarboxylic acid tert-butyl ester (18.5 mmol) is added HCl (4 N) in 1,4-dioxane (185 mmol). The mixture is stirred at room temperature for 1 hour. Hexanes is added to further precipitate the product. The product is filtered off yielding 4-fluoro-thiobenzoic acid hydrazide hydrochloride salt: 1H NMR (400 MHz, CH3OD) δ 7.8-7.75 (m, 2H), 7.09 (t, J=11.6 Hz, 2H). LC/MS: (ES+) 171 (M+1)+.