Réaction #78312

Équation de réaction

N-chlorosuccinimide

Triethylamine

N-chlorosuccinimide

3,5-Dimethylthiophenol

HCl

→

title compound

Rendement 64.0%

N-(3,5-Dimethylphenylthio)succinimide

Rendement 64.0%

Solvants

dichloromethane

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   Autrereaction
3. 3
   workup.STIRRINGwhile stirring for 15 minutes
4. 4
   workup.STIRRINGAfter shaking
5. 5
   Autreorganic layer was dried
6. 6
   Concentrationconcentrated to a small volume
7. 7
   AutreAfter evaporation of the solvent
8. 8
   Autrethe residue was triturated with diethyl ether

Mode opératoire

3,5-Dimethylthiophenol (2.76 g, 0.02 mol) was added by a syringe to an ice cooled mixture of N-chlorosuccinimide (3.34 g, 0.025 mol) and anhydrous dichloromethane (30 mL) under argon atmosphere. After 1 hour, N-chlorosuccinimide (0.4 g, 0.003 mol) was added, then reaction was stirred for 2.5 hours. Triethylamine (3.9 mL, 0.028 mol) was added while stirring for 15 minutes, then dichloromethane and 1N HCl were added. After shaking, organic layer was dried, concentrated to a small volume and passed through a Celite® column. After evaporation of the solvent, the residue was triturated with diethyl ether to give 3.0 g (64%) of title compound, mp 131-134° C. (from diethyl ether).

Source