Water → N-(1-(4-chloromethylphenyl)-1-methylethyl)acetamide

HRID 1282162Notes

Reaction equation

HRID 1282162 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:12][C:13](=[O:15])[CH3:14])([CH3:11])[CH3:10])=[CH:5][CH:4]=1.S(Cl)([Cl:18])=O.O>C(Cl)(Cl)Cl>[Cl:18][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:12][C:13](=[O:15])[CH3:14])([CH3:11])[CH3:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 18423112N-(1-(4-hydroxymethylphenyl)-1-methylethyl)acetamide

Product 1

HCID 18423089N-(1-(4-chloromethylphenyl)-1-methylethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-(1-(4-hydroxymethylphenyl)-1-methylethyl)acetamide (18.24 g) in chloroform (180 ml) was added dropwise thionyl chloride (7.07 ml) over 10 min under ice-cooling and the mixture was stirred at room temperature for 20 hr. The reaction mixture was poured into water (1000 ml) and the organic layer was separated. The organic layer was washed with aqueous sodium hydrogencarbonate and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the title compound (19.17 g) as pale-yellow crystals, m.p.=124-125° C.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washThe organic layer was washed with aqueous sodium hydrogencarbonate and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-ffd84c4fc15a4ffaa897a52fd6d80f36
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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