Hydrochloric Acid → 4-Methoxybenzenecarbothioamide
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewhile being cooled in an ice bath
- distillationThe mixture was then distilled on an oil bath at 100° C
- customAfter the liquid had been removed
- additionaqueous sodium bicarbonate was added
- customthe solid was collected
- customrecrystallized from toluene
Sources & evidence
- ORD record
- ord-e79458266d034204a700be91ab1937be
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04544759
Reaction notes
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