Thiophosgene → HCID 20031847, compound

HRID 231972Notes

Reaction equation

HRID 231972 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[C:7]([S:9][C:10]1[C:15]([F:16])=[C:14]([F:17])[C:13]([F:18])=[C:12]([F:19])[C:11]=1[F:20])=[O:8].[C:24](Cl)([Cl:26])=[S:25]>O.C(Cl)(Cl)Cl>[Cl:26][C:24]([O:3][C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][CH:23]=1)[C:7]([S:9][C:10]1[C:11]([F:20])=[C:12]([F:19])[C:13]([F:18])=[C:14]([F:17])[C:15]=1[F:16])=[O:8])=[S:25]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 14798Sodium HydroxideHCID 57231163HCID 57231163, compound

Product 1

HCID 20031847HCID 20031847, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A solution of 187 mg of sodium hydroxide in 5 ml of water was added to a stirred suspension of S-(pentafluorophenyl) 3-(hydroxy)thiobenzoate (1.0 g) in chloroform (10 ml) at -10° C. Thiophosgene (0.36 ml) was added and the solution stirred whilst being allowed to reach room temperature. The chloroform layer was separated, dried over anhydrous calcium chloride and evaporated to leave a reside which was chromatographed on silica gel using ethyl acetate/hexane mixtures as eluant to give 0.61 g of the title compound.

Workup

  1. customto reach room temperature
  2. customThe chloroform layer was separated
  3. dry with materialdried over anhydrous calcium chloride
  4. customevaporated
  5. customto leave a reside which
  6. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-26029d00e4ac4997a63b252d338f2b7a
Source dataset
uspto-grants-1989_07
Patent number
US04849419

Reaction notes

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