Thionyl Chloride → N-Methyl 4-Methoxybenzimidoyl Chloride

Reaction equation

[CH3:1][NH:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.S(Cl)([Cl:15])=O>>[CH3:1][N:2]=[C:3]([Cl:15])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 3460314-methoxy-N-methylbenzamide

Product 1

HCID 12410495N-Methyl 4-Methoxybenzimidoyl ChlorideYield 76.7%

Procedure

N-Methyl 4-methoxybenzamide (13.95 g, 84.5 mmole) was placed in a 50 ml round bottom flask equipped with magnetic stirrer, heating mantle, condenser and base trap. Thionyl chloride (33 g, 278 mmole) was added. The reaction was stirred and heated at reflux until gas evolution ceased (three hours). The excess thionyl chloride was distilled at ca. 15 mm Hg, and the product distilled at 75°-80° C. (0.1 mm Hg) to yield 11.9 g (76%) of the title compound as a clear colorless liquid.

Workup

customequipped with magnetic stirrer
temperatureheating mantle, condenser and base trap
temperatureheated
temperatureat reflux until gas evolution
custom(three hours)
distillationThe excess thionyl chloride was distilled at ca. 15 mm Hg
distillationthe product distilled at 75°-80° C. (0.1 mm Hg)

Sources & evidence

ORD record: ord-4883742856d94c599313418f15ed2269
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04528382

Reaction notes

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