Chloroacetyl chloride → 2-chloro-N-[(dimethylcarbamoyl)methyl]acetamide

HRID 359065Notes

Reaction equation

HRID 359065 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][N:7]([CH3:12])[C:8](=[O:11])[CH2:9][NH2:10].C(N(CC)CC)C>ClCCl>[CH3:6][N:7]([CH3:12])[C:8](=[O:11])[CH2:9][NH:10][C:3](=[O:4])[CH2:2][Cl:1]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 49618232-amino-N,N-dimethylacetamide

Product 1

HCID 95040152-chloro-N-[(dimethylcarbamoyl)methyl]acetamideYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of chloroacetyl chloride (1.7 g) in dichloromethane was stirred in an ice-bath, while a solution of N,N-dimethylglycinamide (1.8 g) and triethylamine (2.2 ml) in dichloromethane (20 ml) was added over 20 minutes. The reaction mixture was stirred for 30 minutes and was then washed with water (2×10 ml), and dried over MgSO4. The solution was evaporated under reduced pressure. Thus was obtained N,N-dimethyl chloroacetylglycinamide (2.0 g) as a brown oil, which was used directly, and without further purification.

Workup

  1. additionwas added over 20 minutes
  2. washwas then washed with water (2×10 ml)
  3. dry with materialdried over MgSO4
  4. customThe solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fce9bd1b893b4aa5ad609571ed111a76
Source dataset
uspto-grants-1991_03
Patent number
US04999377

Reaction notes

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