Thionyl Chloride → N-Methyl 4-Chlorobenzimidoyl Chloride

Reaction equation

[CH3:1][NH:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([Cl: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]([Cl:10])=[CH:6][CH:5]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 101339Benzamide, 4-chloro-N-methyl-

Product 1

HCID 12341506N-Methyl 4-Chlorobenzimidoyl ChlorideYield 83.4%

Procedure

N-Methyl 4-chlorobenzamide (42.6 g, 251 mmole) and thionyl chloride (153.3 g, 1.28 mole) were reacted as in Example I to yield 39.3 g (83.4%) of the title compound, b.p. 125° C. (15 mm Hg).

Sources & evidence

ORD record: ord-aa49b43da37c4071bcf1eef74fe1037b
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04528382

Reaction notes

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