Thionyl Chloride → N-((4-(chloromethyl)phenyl)methyl)acetamide

HRID 1595374Notes

Reaction equation

HRID 1595374 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15550683N-(4-(hydroxymethyl)benzyl)acetamide

Product 1

HCID 15550682N-((4-(chloromethyl)phenyl)methyl)acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-(4-hydroxymethylphenylmethyl)acetamide (1.5 g) in chloroform (50 ml) was added thionyl chloride (0.73 ml) and the mixture was refluxed under heating for 1 hr. The solvent was evaporated and the obtained residue was crystallized from ethyl acetate to give the objective N-(4-chloromethylphenylmethyl)acetamide (1.8 g) as pale-yellow crystals, melting point 116-118° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1 hr
  3. customThe solvent was evaporated
  4. customthe obtained residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-45ec43753e69468cb70187982f308366
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

Loading…