Carbon Disulfide → HCID 178519452, compound

Participants

Reaction Steps

To a solution of 4-(hydroxymethyl)benzoic hydrazide CAS [58855-42-8] (1.4 g, 8.4 mmol) in ethanol (14 mL) were added carbon disulfide (1.12 mL, 18.5 mmol) and triethyl amine (1.3 mL, 9.3 mmol). After heating to reflux for 16 h with stirring, the reaction mixture was cooled to RT and diluted with ethyl acetate. The mixture was washed with 10% HCl solution and brine, dried over magnesium sulfate, and concentrated. Purification of the residue by MPLC (65% ethyl acetate in hexanes) gave 1.62 g of [4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl]methanol as a colorless solid. 1H NMR (600 MHz, CD3OD) δ 7.90 (ddd, J=0.59, 2.05, 8.51 Hz, 2H), 7.54 (d, J=7.92 Hz, 2H), 4.68 (s, 2H)

Provenance & Evidence