4-Isopropylbenzoic Acid → HCID 86624588, compound

Participants

Reaction Conditions

Reaction Steps

To a toluene (25 mL) solution of methyl 4-[2-(4-isopropylbenzoyl)hydrazino]benzoate (0.94 g, 3.0 mmol), prepared from 4-methoxycarbonylphenylhydrazine and 4-isopropylbenzoic acid using the coupling technique described above, is added Lawesson's Reagent (1.82 g, 4.5 mmol). The mixture is stirred at 120° C. for 10 hr and cooled to room temperature. The precipitate is removed and the filtrate is concentrated, chromatographed (silica gel, 1:9 ethyl acetate-hexane) to give an intermediate compound, MS (ES+): m/e 496. The intermediate is then treated with NaOH (1.25N, 2.63 mL, 3.3 mmol) in THF (20 mL) at 65° C. for 1 h. The solvent is then replaced with ether (50 mL), and the mixture is washed with water, dried and chromatographed to provide the thiohydrazide, methyl 4-{2-[(4-isopropylphenyl)carbonothioyl]hydrazino}benzoate (0.82 g, 81%). MS (ES+): m/e 329.

Provenance & Evidence