Thionyl Chloride → N-Cyclohexyl 4-Chlorobenzimidoyl Chloride

HRID 370915Notes

Reaction equation

HRID 370915 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

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 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

  1. temperatureat reflux
  2. customExcess thionyl chloride was removed by distillation

Sources & evidence

ORD record
ord-1a7be2027218483d9b1209200e215c66
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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