Thionyl Chloride → N-Methyl 4-Methylbenzimidoyl Chloride

HRID 370910Notes

Reaction equation

HRID 370910 reaction equation
[CH3:1][NH:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.S(Cl)([Cl:14])=O>>[CH3:1][N:2]=[C:3]([Cl:14])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 140377N-Methyl-p-toluamide

Product 1

HCID 12410496N-Methyl 4-Methylbenzimidoyl ChlorideYield 80%

Procedure

N-Methyl 4-methylbenzamide (10.02 g, 67.2 mmole) was treated with thionyl chloride (31.7 g, 267 mmole) as in Example I. Gas evolution ceased after the reaction had been heated for 45 minutes. The product was isolated as in Example I to yield 9.0 g (80%) of the title compound as a clear colorless liquid, b.p. 57° C. (~0.1 mm Hg).

Workup

  1. temperaturehad been heated for 45 minutes
  2. customThe product was isolated as in Example I

Sources & evidence

ORD record
ord-2c187e162997469ab1326661be35710b
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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