Hydrochloric Acid → 4-Chlorothiobenzamide

HRID 463882Notes

Reaction equation

HRID 463882 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(N)(=[S:12])C.Cl>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH2:7])=[S:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 121634-ChlorobenzonitrileHCID 2723949Thioacetamide

Product 1

HCID 27348264-ChlorothiobenzamideYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 55.03 g of 4-chlorobenzonitrile, 75.13 g of thioacetamide and 600 ml of dimethylformamide was saturated with dry hydrogen chloride gas while being chilled in an ice bath. The mixture was then distilled slowly on an oil bath at 100° C. When the liquid had been removed, aqueous sodium bicarbonate was added. The solid was collected and recrystallized from toluene, giving 48.35 g of 4-chlorothiobenzamide as yellow crystals.

Workup

  1. temperaturewhile being chilled in an ice bath
  2. distillationThe mixture was then distilled slowly on an oil bath at 100° C
  3. customWhen the liquid had been removed
  4. additionaqueous sodium bicarbonate was added
  5. customThe solid was collected
  6. customrecrystallized from toluene

Sources & evidence

ORD record
ord-779b64027b4342e8b5465d74100591ca
Source dataset
uspto-grants-1985_10
Patent number
US04544759

Reaction notes

Loading…