Hydrochloric Acid → 4-hydroxymethyl-3-(2,3,4-trifluorophenyl)-2(3H)-thiazolethione

Triethylammonium N-(2,3,4-trifluorophenyl)dithiocarbamate (81.2 g) prepared in the same manner as in Reference Example 1 was added to ethanol (800 ml) and thereto 1-acetoxy-3-chloroacetone (37.7 g) was added dropwise at 5° to 7° C. with stirring over a period of 20 minutes. After stirring the mixture for 50 minutes, 10% solution of hydrogen chloride in ethanol (240 ml) was added and the mixture was refluxed for 3 hours. After the solvent was distilled off under the reduced pressure, cooled water was added to the residue and resultant was extracted with chloroform. The extract was washed with a NaCl solution and dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. The residue was recrystallized from a mixed solvent of hexane-ethyl acetate to give the title compound (59 g) as pale yellow crystals. The compound had physical properties identical to those of 4-hydroxymethyl-3-(2,3,4-trifluorophenyl)-2(3H)-thiazolethione prepared in the above Reference Example 18.

1. stirringAfter stirring the mixture for 50 minutes
2. temperaturethe mixture was refluxed for 3 hours
3. distillationAfter the solvent was distilled off under the reduced pressure
4. temperaturecooled water
5. additionwas added to the residue and resultant
6. extractionwas extracted with chloroform
7. washThe extract was washed with a NaCl solution
8. dry with materialdried over anhydrous sodium sulfate
9. distillationby distilling off the solvent under reduced pressure
10. customThe residue was recrystallized from a mixed solvent of hexane-ethyl acetate

ORD record

ord-ecb597a991c54c4fb78280f6fc24cc85

Source dataset

uspto-grants-1989_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04853469