Trichloroethanol → HCID 131725384, compound

Participants

Reaction Conditions

Reaction Steps

Diphenylphosphonic azide (0.88mL, 4.0 mmol) was added dropwise to a mixture of isothiazole-5-carboxylic acid (500 mg, 3.90 mmol) and triethylamine (0.57 mL, 4.1 mmol) in toluene (10 mL) at rt and the resulting turbid, yellow solution was heated at 60° C. for 1 h. 2,2,2-Trichloroethanol (0.56 mL, 5.8 mmol) was introduced and the temperature was raised to 100° C. for an additional 3 h. The mixture was then cooled to rt, poured into water, extracted with ethyl acetate (3×) and the combined organics were washed with saturated sodium chloride aqueous solution and dried (MgSO4). Concentration in vacuo and flash chromatography of the residue on silica gel eluting with a mixture of ethyl acetate and hexanes (1:3) provided 553 mg of 2,2,2-trichloroethylisothiazol-5-ylcarbamate as a faint yellow powder.

Provenance & Evidence