Reaction #52156

Reaction equation

SOCl2

N-(3,5-Dichlorobenzenesulfonyl)-octahydroisoindole-1-carboxylic acid

→

N-(3,5-dichlorobenzenesulfonyl)-octahydroisoindole-1-carboxylic acid chloride

Solvents

CH2Cl2

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was refluxed under nitrogen for ˜1 hr
2. 2
   ConcentrationThe reaction mixture was then concentrated in vacuo
3. 3
   Otherazeotroped with toluene (1×5 mL)

Procedure

N-(3,5-Dichlorobenzenesulfonyl)-octahydroisoindole-1-carboxylic acid (1 gm, 2.64 mmol) was dissolved in CH2Cl2 (5 mL) containing DMF (1 drop) and SOCl2 (770 μL, 10.56 mmol). The reaction mixture was refluxed under nitrogen for ˜1 hr. The reaction mixture was monitored by TLC for the formation of the acid chloride. The reaction mixture was then concentrated in vacuo and azeotroped with toluene (1×5 mL) to afford N-(3,5-dichlorobenzenesulfonyl)-octahydroisoindole-1-carboxylic acid chloride which was used without further purification in the subsequent step.

Source