Thionyl Chloride → N-(2-Chloroethyl)-N-methylbenzylamine hydrochloride
Reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([N:12]([CH3:16])[CH2:13][CH2:14]O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)C>[ClH:3].[CH2:5]([N:12]([CH2:13][CH2:14][Cl:3])[CH3:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The procedure of Hall, et al.[Organic Syntheses Coll. Vol. 4, 1963, 333-335] was used. To thionyl chloride (22.92 mL, 03.14 mol) at 0° C. was added dropwise N-benzyl-N-methyl ethanolamine (50 g, 0.303 mol). The creamy, off-white material was stirred for 1 hour at 0° C. and then 1 hour at room temperature. Anhydrous ethanol (129 mL) was added to the material. The solution was refluxed for 20 minutes and then was concentrated to an off-white solid. The solid was triturated with Et2O to give the title compound as a white solid (62.51 g, 94% yield, mp 136-138° C.).