Thionyl Chloride → N-Octyl 4-Chlorobenzimidoyl Chloride

HRID 370916Notes

Reaction equation

HRID 370916 reaction equation
[CH2:1]([NH:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].S(Cl)([Cl:21])=O>>[CH2:1]([N:9]=[C:10]([Cl:21])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 17219574-chloro-N-octylbenzamide

Product 1

HCID 13477601N-Octyl 4-Chlorobenzimidoyl ChlorideYield 77%

Procedure

N-Octyl 4-chlorobenzamide (17.2 g, 64.2 mmole) and thionyl chloride (42.59 g, 358 mmole) were stirred and heated at reflux for one hour. The product was isolated by fractional distillation at reduced pressure (b.p. 70°-90° C. at 15 mm Hg) to yield 14.0 g (77%) of impure title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for one hour
  3. customThe product was isolated by fractional distillation at reduced pressure (b.p. 70°-90° C. at 15 mm Hg)

Sources & evidence

ORD record
ord-d8717f55b0014481a130076770b05e2f
Source dataset
uspto-grants-1985_07
Patent number
US04528382

Reaction notes

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