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

HRID 1722077Notes

Reaction equation

HRID 1722077 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[S:21])[S:12][CH2:13][C:14](=O)[CH2:15][O:16]C(=O)C.Cl>C(O)C>[OH:16][CH2:15][C:14]1[N:10]([C:3]2[CH:4]=[CH:5][C:6]([F:9])=[C:7]([F:8])[C:2]=2[F:1])[C:11](=[S:21])[S:12][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 200303133-acetoxy-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamate

Product 1

HCID 146733094-hydroxymethyl-3-(2,3,4-trifluorophenyl)-2(3H)-thiazolethioneYield 68.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3-Acetoxy-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamate (1.0 g) prepared in the previous Reference Example was added to ethanol (15 ml) and thereto 10% solution of hydrogen chloride in ethanol (5 ml) was added and the mixture was refluxed for one hour and 30 minutes. After the solvent was distilled off under reduced pressure, cooled water was added to the residue and the resultant was extracted with chloroform. After the extract was washed with a NaCl solution and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane-ethyl acetate to give the title compound (0.56 g) as pale yellow crystals, m.p. 113°-116° C.

Workup

  1. temperaturethe mixture was refluxed for one hour and 30 minutes
  2. distillationAfter the solvent was distilled off under reduced pressure
  3. temperaturecooled water
  4. additionwas added to the residue
  5. extractionthe resultant was extracted with chloroform
  6. washAfter the extract was washed with a NaCl solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was recrystallized from a mixed solvent of hexane-ethyl acetate

Sources & evidence

ORD record
ord-66403e29b0d14226aaf9020986cc93f9
Source dataset
uspto-grants-1989_08
Patent number
US04853469

Reaction notes

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