Ethyl Acetate → HCID 19900665, compound

Participants

Reaction Steps

Thiophosgene (0.39 mL, 5.1 mmol) is added dropwise to a -78° C. solution of S-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl] hydrazinecarbothioate (1.5 g, 5.1 mmol) in tetrahydrofuran (150 mL). The reaction mixture is stirred for 10 minutes then poured into a separatory funnel containing ethyl acetate and aqueous sodium bicarbonate. The organic phase is washed three times with water and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a solid which is crystallized from dichloromethane/hexane affording 1.1 g (62%) of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1,3,4-oxadiazole-2(3H)-thione, mp 129.0°-131.0° C.

Provenance & Evidence