Trichloroethanol → HCID 131725384, compound

Temperature

60 °C

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.

1. temperaturethe temperature was raised to 100° C. for an additional 3 h
2. temperatureThe mixture was then cooled to rt
3. extractionextracted with ethyl acetate (3×)
4. washthe combined organics were washed with saturated sodium chloride aqueous solution
5. dry with materialdried (MgSO4)
6. concentrationConcentration in vacuo and flash chromatography of the residue on silica gel eluting
7. additionwith a mixture of ethyl acetate and hexanes (1:3)

ORD record

ord-4f506077a03f4e5391516d3ea9a046e3

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07012075B2