Hydrochloric Acid → HCID 19900655, compound

Participants

Reaction Steps

A 12.5% solution of phosgene in toluene (8.6 mL, 9.6 mmol) is added dropwise to a -78° C. solution of 3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl hydrazinecarbodithioate (1.5 g, 4.8 mmol) and N,N-diisopropylethylamine (3.3 mL, 19.2 mmol) in tetrahydrofuran (150 mL). The reaction mixture is stirred for 10 minutes then poured into a separatory funnel containing ethyl acetate and water. The pH of the aqueous phase is adjusted to 3 with 1N hydrochloric acid. The organic phase is washed twice with water, then with a saturated solution of sodium bicarbonate followed by brine. Drying over magnesium sulfate and evaporation of the solvents gives a solid which is crystallized twice from isopropyl ether/hexane to afford 0.7 g (43%) of 5-[[3,5-bis(1,1-dimethylethyl) -4-hydroxyphenyl]thio]-1,3,4-thiadiazol-2(3H)-one, mp 194°-197° C. (dec).

Provenance & Evidence