Hydrochloric Acid → 2(3H)-Thiazolethione, 4-(chloromethyl)-3-(2,3,4-trifluorophenyl)-

HRID 1085308Notes

Reaction equation

HRID 1085308 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].Cl>CO>[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 100869643-chloro-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Chloro-2-oxopropyl N-(2,3,4-trifluorophenyl)dithiocarbamate (4.0 g) prepared in the same manner as in Reference Example 6 was added to 30% HCl in methanol (15 ml) and the mixture was refluxed for 3 hours. The solvent was distilled off under reduced pressure and to the residue was added cooled water and the solution was extracted with chloroform. The extract was washed with a NaCl solution, dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was recrystallized from cyclohexane to give the title compound (2.6 g) as pale yellow crystals, m.p. 127°-130° C.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. distillationThe solvent was distilled off under reduced pressure and to the residue
  3. additionwas added
  4. temperaturecooled water
  5. extractionthe solution was extracted with chloroform
  6. washThe extract was washed with a NaCl solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-a8918bf02a3c494689d76a144cbbe8ef
Source dataset
uspto-grants-1991_04
Patent number
US05008389

Reaction notes

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