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

HRID 1816025Notes

Reaction equation

HRID 1816025 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-4b94cf480e324b40b3df2380f045f33c
Source dataset
uspto-grants-2005_04
Patent number
US06881846B2

Reaction notes

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