Thionyl Chloride → 4-Chloro-2-(4-methylphenyl)benzonitrile

HRID 1728569Notes

Reaction equation

HRID 1728569 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=O)=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH:7]=1>>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]#[N:12])=[C:8]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 224179884-Chloro-2-(4-methylphenyl)benzamide

Product 1

HCID 224179974-Chloro-2-(4-methylphenyl)benzonitrile

Procedure

26 ml of thionyl chloride was dropwise added to 8.9 g of 4-chloro-2-(4-methylphenyl)benzamide, and the mixture was heated under reflux for 2.5 hr. Excess thionyl chloride was distilled off as much as possible by making use of toluene. The residue was recrystallized from a mixed solvent of tetrahydrofuran-isopropyl ether-n-hexane to prepare 7.2 g of a product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hr
  3. distillationExcess thionyl chloride was distilled off as much as possible
  4. customThe residue was recrystallized from a mixed solvent of tetrahydrofuran-isopropyl ether-n-hexane
  5. customto prepare 7.2 g of a product

Sources & evidence

ORD record
ord-d11a82af90d64ab1ba9762c9e61a0fe0
Source dataset
uspto-grants-1994_07
Patent number
US05328911

Reaction notes

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