Thionyl Chloride → N-(4-(1-chloroethyl)phenylmethyl)acetamide

HRID 1282057Notes

Reaction equation

HRID 1282057 reaction equation
O[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:6][CH:5]=1)[CH3:3].S(Cl)([Cl:17])=O>C(Cl)(Cl)Cl>[Cl:17][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:6][CH:5]=1)[CH3:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18423003HCID 18423003, compound

Product 1

HCID 18423036N-(4-(1-chloroethyl)phenylmethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-{[4-(1-hydroxyethyl)phenyl]methyl}acetamide (5.7 g) and thionyl chloride (2.6 ml) in chloroform (50 ml) was refluxed under heating for 1.5 hr. The solvent was evaporated to give a brown oil (6.7 g). The obtained brown oil was purified by silica gel column chromatography (developing solvent; chloroform:methanol=20:1) to give the title compound (5.5 g) as a pale-brown oil.

Workup

  1. temperatureunder heating for 1.5 hr
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-587b739f98f14db3a7b89b05d50dd930
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

Loading…