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

HRID 57217Notes

Reaction equation

HRID 57217 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-5566117e5a23432883496a6c102eaef6
Source dataset
uspto-grants-2016_09
Patent number
US09434718B2

Reaction notes

Loading…