Thionyl Chloride → 4-Cyclohexylbenzoyl chloride

HRID 1249980Notes

Reaction equation

HRID 1249980 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 dichloromethane. 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-b93010bd7abf426d961f5628aacf8c91
Source dataset
uspto-grants-2002_01
Patent number
US06335327B1

Reaction notes

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