Thiophosgene → HCID 11724583, compound

Participants

Reaction Steps

Thiophosgene (0.10 mL, 1.36 mmol) is added dropwise to a -78° C. solution of [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy-acetic acid hydrazide (0.40 g, 1.36 mmol) in tetrahydrofuran (25 mL). The reaction mixture is stirred for 30 minutes, diluted with ethyl acetate, and washed three times with water and once with brine. Drying the organic phase over magnesium sulfate and evaporation gives a pale yellow oil which is crystallized from ethyl acetate/hexane yielding 0.36 g (78%) of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxymethyl]-1,3,4-oxadiazole-2(3H)-thione, mp 195.0°-196.5° C.

Provenance & Evidence