Thionyl Chloride → 4-Cyclohexylbenzoyl chloride

HRID 1870445Notes

Reaction equation

HRID 1870445 reaction equation
[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:18])=O>>[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([Cl:18])=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 883374-Cyclohexylbenzoic acid

Product 1

HCID 218908474-Cyclohexylbenzoyl chloride

Procedure

To 4-cyclohexylbenzoic acid (2 g) is added thionyl chloride (20 ml), and the mixture is refluxed for two hours. The mixture is evaporated to remove the thionyl chloride to give 4-cyclohexylbenzoyl chloride. To a solution of 5-ethoxycarbonylmethyl-7-chloro-2,3,4,5-tetrahydro-1H-benzazepine (2.2 g) in dichloromethane (50 ml) is added pyridine (3.3 g), and to the mixture is added with stirring the above obtained 4-cyclohexylbenzoyl chloride under ice-cooling, and the mixture is stirred at room temperature overnight. To the reaction solution is added water, and the mixture is extracted with dichloro-methane. The extract is washed with diluted hydrochloric acid, and washed with water, and dried over magnesium sulfate. The mixture is evaporated to remove the solvent, and the residue is purified by silica gel column chromatography (solvent; dichloromethane) to give 5-ethoxycarbonylmethyl-7-chloro-1-(4-cyclohexylbenzoyl)-2,3,4,5-tetrahydro-1H-benzazepine (4 g) as colorless oil.

Workup

  1. temperaturethe mixture is refluxed for two hours
  2. customThe mixture is evaporated
  3. customto remove the thionyl chloride

Sources & evidence

ORD record
ord-150bd7f395ed4eb8b3e62d47fdb2cba5
Source dataset
uspto-grants-2000_08
Patent number
US06096735

Reaction notes

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