Hydrochloric Acid → 4-Methoxybenzenecarbothioamide

HRID 463884

Reaction equation

HRID 463884 reaction equation
[C:1](#[N:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(N)(=[S:13])C.Cl>CN(C)C=O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:1]([NH2:10])=[S:13])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 701294-MethoxybenzonitrileHCID 2723949Thioacetamide

Product 1

HCID 7368274-MethoxybenzenecarbothioamideYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 53.26 g of anisonitrile and 60.10 g of thioacetamide in 600 ml of dimethylformamide was saturated with dry hydrogen chloride gas while being cooled in an ice bath. The mixture was then distilled on an oil bath at 100° C. After the liquid had been removed, aqueous sodium bicarbonate was added and the solid was collected and recrystallized from toluene, giving 50.47 g of 4-methoxythiobenzamide as a yellow solid.

Workup

  1. temperaturewhile being cooled in an ice bath
  2. distillationThe mixture was then distilled on an oil bath at 100° C
  3. customAfter 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-e79458266d034204a700be91ab1937be
Source dataset
uspto-grants-1985_10
Patent number
US04544759

Linked notes

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