Hydrochloric Acid → HCID 54090446, compound

Participants

Reaction Conditions

Reaction Steps

Thiophosgene (1.6 mL, 21.0 mmol) is added dropwise to a -78° C. solution of 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol (5.0 g, 21.0 mmol) and N,N-diisopropylethylamine (5.4 mL, 31.4 mmol) in toluene/dichloromethane (100 mL/20 mL). The reaction mixture is stirred for 1.5 hours then poured into a separatory funnel containing ethyl acetate and water. The aqueous phase is acidified to pH 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 the organic phase over magnesium sulfate and evaporation of the solvents gives a crude product which is dissolved in dichloromethane (200 mL) and cooled to 0° C. Hydrazine monohydrate (1.5 mL, 31.0 mmol) is added in three portions at 30 minute intervals, and the solution is stirred for 1 hour. The reaction is poured into ethyl acetate and washed four times with an aqueous solution of sodium chloride and once with a saturated solution of sodium chloride. Drying the organic phase over magnesium sulfate and evaporation gives an amorphous solid which is crystallized from 50 mL of ethyl acetate/hexane (5/95) affording 3.5 g (53% from 2,6-bis(1,1-dimethylethyl)-4-mercaptophenol) of 3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl hydrazinecarbodithioate, mp 145.5°-146.0° C.

Provenance & Evidence