Water → N-((4-chloromethyl-2,6-dimethylphenyl)methyl)acetamide

HRID 1282064Notes

Reaction equation

HRID 1282064 reaction equation
O[CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[C:5]([CH3:15])[CH:4]=1.S(Cl)([Cl:18])=O.O>ClCCl>[Cl:18][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[C:5]([CH3:15])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 18423136N-((4-hydroxymethyl-2,6-dimethylphenyl)methyl)acetamide

Product 1

HCID 18423130N-((4-chloromethyl-2,6-dimethylphenyl)methyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-((4-hydroxymethyl-2,6-dimethylphenyl)methyl)acetamide (1.0 g) in dichloromethane (12 ml) was added thionyl chloride (0.88 ml). This mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was recrystallized from ethyl acetate-isopropyl ether to give the title compound (1.0 g) as white crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with aqueous sodium hydrogencarbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe obtained residue was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-1de72c86f6dc48e18196c7cebf295018
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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