Benzene → HCID 20385656, compound

HRID 46772Notes

Reaction equation

HRID 46772 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([S:17][C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=2)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH:29]1C=CC=C[CH:30]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([S:17][C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)=[C:11]([CH2:13][C:14]([O:16][CH2:29][CH3:30])=[O:15])[N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 20385666HCID 20385666, compound

Product 1

HCID 20385656HCID 20385656, compound

Procedure

To 1.0 g of 2-p-chlorophenyl-5-p-chlorophenylthio-4-thiazoleacetic acid were added 10 ml of benzene and 2.0 ml of thionyl chloride, and the mixture was refluxed for 30 minutes. The solvent and the excess thionyl chloride were distilled off under reduced pressure. To the residue was added 20 ml of ethanol and stirred at room temperature for 1 hour and then the solvent was distilled off under reduced pressure. Recrystallization of the residue from ethanol gave 0.8 g of the title compound, melting at 103°-104° C.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. distillationThe solvent and the excess thionyl chloride were distilled off under reduced pressure
  3. additionTo the residue was added 20 ml of ethanol
  4. distillationthe solvent was distilled off under reduced pressure
  5. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-7be32261ce814412ab8448adaa23e835
Source dataset
uspto-grants-1979_11
Patent number
US04175130

Reaction notes

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