Thionyl Chloride → N-Cyclohexyl 4-Chlorobenzimidoyl Chloride

Reaction equation

[CH:1]1([NH:7][C:8](=O)[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:19])=O>>[CH:1]1([N:7]=[C:8]([Cl:19])[C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 2254614-Chloro-N-cyclohexylbenzamide

Product 1

HCID 13477600N-Cyclohexyl 4-Chlorobenzimidoyl Chloride

Procedure

N-Cyclohexyl 4-chlorobenzamide (12.8 g, 53.9 mmole) and thionyl chloride (43.14 g, 363 mmole) were heated at reflux with stirring for 1.75 hours. Excess thionyl chloride was removed by distillation. The title compound was isolated by distillation (b.p. 130° C. at ~15 mm Hg) to yield 7.4 g (54%) of a clear colorless liquid which crystallized upon cooling.

Workup

temperatureat reflux
customExcess thionyl chloride was removed by distillation

Sources & evidence

ORD record: ord-1a7be2027218483d9b1209200e215c66
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04528382

Reaction notes

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