3-chloro-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamate → 2(3H)-Thiazolethione, 4-(chloromethyl)-3-(2,3,4-trifluorophenyl)-

HRID 1612952Notes

Reaction equation

HRID 1612952 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:18])[S:12][CH2:13][C:14](=O)[CH2:15][Cl:16].[H][H]>>[Cl: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:18])[S:12][CH:13]=1

Participants

3

Reactant 2

HCID 100869643-chloro-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 41903592(3H)-Thiazolethione, 4-(chloromethyl)-3-(2,3,4-trifluorophenyl)-Yield 69%

Procedure

3-Chloro-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamate (4.0 g) is added to 30% hydrogen chloridemethanol solution (15 ml), and the mixture is refluxed for 3 hours. The solvent is distilled off under reduced pressure, and cold water is added to the residue and the mixture is extracted with chloroform. The extract is washed with saline solution, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue is recrystallized from cyclohexane to give the title compound (2.6 g) as pale yellow crystals.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. distillationThe solvent is distilled off under reduced pressure, and cold water
  3. additionis added to the residue
  4. extractionthe mixture is extracted with chloroform
  5. washThe extract is washed with saline solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customThe residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-e7b5afb0fa6541abbe53a9e28c6f25f9
Source dataset
uspto-grants-1993_03
Patent number
US05191079

Reaction notes

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