4-Chloro-N-(1-methylethyl)benzamide → N-Isopropyl 4-Chlorobenzimidoyl Chloride

HRID 370914Notes

Reaction equation

HRID 370914 reaction equation
[CH:1]([NH:4][C:5](=O)[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)([CH3:3])[CH3:2].S(Cl)([Cl:16])=O>>[CH:1]([N:4]=[C:5]([Cl:16])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 240454-Chloro-N-(1-methylethyl)benzamideHCID 24386Thionyl Chloride

Product 1

HCID 12582456N-Isopropyl 4-Chlorobenzimidoyl Chloride

Procedure

N-Isopropyl 4-chlorobenzamide (12.7 g, 64.3 mmole) and thionyl chloride (53.81 g, 447 mmole) were heated at reflux with stirring for two hours. Excess thionyl chloride was removed by distillation. The title compound was isolated by distillation (b.p. 65°-70° C. at ~1 mm Hg) to yield 10.7 g (77%) of a light brown yellow liquid.

Workup

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

Sources & evidence

ORD record
ord-b2a44d9e97fb44039cf3f9aabac53208
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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