Chloroacetyl chloride → N-benzyl-2-chloro-N-methylacetamide

HRID 335540

Reaction equation

HRID 335540 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:10][CH2:11][C:12](Cl)=[O:13]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[CH2:3]([N:2]([CH3:1])[C:12](=[O:13])[CH2:11][Cl:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 7669N-Methylbenzylamine

Product 1

HCID 4639192N-benzyl-2-chloro-N-methylacetamideYield 63.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a vigorously stirred suspension of N-methylbenzylamine (0.260 mL, 2 mmol) in EtOAc (3 mL) and 3 mL of saturated NaHCO3 solution was added chloroacetyl chloride (0.160 mL, 2 mmol). Effervescence was observed. Once gas production had ceased, the reaction mixture was diluted with hexanes (10 mL). The phases were separated and the organic phase was washed with brine (5 mL), dried and concentrated to yield ˜0.250 g of the title compound as an oil. The crude material was used in the subsequent step without further purification.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with brine (5 mL)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-530428ae848045debcd1e14d8f8416a2
Source dataset
uspto-grants-2014_11
Patent number
US08884034B2

Linked notes

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