Thiophosgene → S-(2,4,5-Trichlorophenyl) 4-(chlorothiocarbonyloxy)thiobenzoate

HRID 231955Notes

Reaction equation

HRID 231955 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([S:8][C:9]2[CH:14]=[C:13]([Cl:15])[C:12]([Cl:16])=[CH:11][C:10]=2[Cl:17])=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].[C:22](Cl)([Cl:24])=[S:23]>C(Cl)(Cl)Cl.O>[Cl:24][C:22]([O:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([S:8][C:9]2[CH:14]=[C:13]([Cl:15])[C:12]([Cl:16])=[CH:11][C:10]=2[Cl:17])=[O:7])=[CH:4][CH:3]=1)=[S:23]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 14798Sodium HydroxideHCID 86743245S-(2,4,5-Trichlorophenyl) 4-(hydroxy)thiobenzoate

Product 1

HCID 86743246S-(2,4,5-Trichlorophenyl) 4-(chlorothiocarbonyloxy)thiobenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

S-(2,4,5-Trichlorophenyl) 4-(hydroxy)thiobenzoate (5.4 g) in dry chloroform (70 ml) at -20° C. was treated sequentially with sodium hydroxide (0.78 g) in water (3 ml) and thiophosgene (1.85 ml). The solution was allowed to warm to room temperature and was stirred for a further 2 hours. The reaction mixture was then dried over calcium chloride and the filtered solution evaporated to give a crude solid. Purification by chromatography on silica gel using ethyl acetate/hexane mixtures as eluants afforded 3.4 g of the title compound.

Workup

  1. dry with materialThe reaction mixture was then dried over calcium chloride
  2. customthe filtered solution evaporated
  3. customto give a crude solid
  4. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-3e4005e40ba543a0bb8972fa85acbdec
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

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