Dichloroacetyl chloride → N-methyl-N-formyl-alpha,alpha-dichloroacetamide

HRID 1825903Notes

Reaction equation

HRID 1825903 reaction equation
[Cl:1][CH:2]([Cl:6])[C:3](Cl)=[O:4].[CH3:7][NH:8][CH:9]=[O:10]>C(Cl)(Cl)Cl>[CH3:7][N:8]([CH:9]=[O:10])[C:3](=[O:4])[CH:2]([Cl:6])[Cl:1]

Participants

4

Reactant 2

HCID 6593Dichloroacetyl chlorideHCID 31254N-Methylformamide

Product 1

HCID 22139966N-methyl-N-formyl-alpha,alpha-dichloroacetamideYield 86%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

25 g of dichloroacetyl chloride (1.25 eq.) was added to a solution of 50 g N-methylformamide (NMF) in chloroform at ambient temperature. The reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate, dried with magnesium sulfate and the solvent was evaporated off in vacuum to give N-methyl-N-formyl-α,α-dichloroacetamide (86% yield) in high purity as a yellow oil. The chemical structure was confirmed by APCI-MS, FT-IR, 1H and 13C magnetic resonance spectroscopy.

Workup

  1. washThe reaction mixture was washed with an aqueous solution of sodium hydrogencarbonate
  2. dry with materialdried with magnesium sulfate
  3. customthe solvent was evaporated off in vacuum

Sources & evidence

ORD record
ord-b8dbbde7979248c1a0e3a7611dca2425
Source dataset
uspto-grants-2006_05
Patent number
US07049338B2

Reaction notes

Loading…