4-Chlorobenzamide → 4-Chlorothiobenzamide

HRID 2232382Notes

Reaction equation

HRID 2232382 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=O)=[CH:4][CH:3]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:20]2)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:20])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 120844-ChlorobenzamideHCID 87949Lawesson's reagent

Product 1

HCID 27348264-ChlorothiobenzamideYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred mixture of 14.9 grams (0.102 mole) of 4-chlorobenzamide in 800 ml of toluene was added 20.6 grams (0.051 mole) of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (Lawesson's Reagent). This mixture was stirred and heated at reflux for two hours. The reaction mixture was allowed to cool slowly to room temperature. Approximately 600 ml of toluene was evaporated from the mixture under reduced pressure, leaving a residual liquid. This liquid was purified by column chromatography on silica gel, eluting with methylene chloride:ethyl acetate (60:40), to yield 5.6 grams of 4-chlorophenylthiocarboxamide as a solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for two hours
  3. customApproximately 600 ml of toluene was evaporated from the mixture under reduced pressure
  4. customleaving a residual liquid
  5. customThis liquid was purified by column chromatography on silica gel
  6. washeluting with methylene chloride:ethyl acetate (60:40)

Sources & evidence

ORD record
ord-5a50790b1e0340a1aa3a9f1003fdbbc8
Source dataset
uspto-grants-1988_11
Patent number
US04788207

Reaction notes

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