Bromoacetyl bromide → Acetamide, 2-bromo-N-methyl-N-2-propynyl-

HRID 267820Notes

Reaction equation

HRID 267820 reaction equation
[CH3:1][NH:2][CH2:3][C:4]#[CH:5].[Br:6][CH2:7][C:8](Br)=[O:9].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CCOCC>[CH3:1][N:2]([CH2:3][C:4]#[CH:5])[C:8](=[O:9])[CH2:7][Br:6]

Participants

6

Conditions

Temperature
25 °C

Procedure

A solution of 13.8 g (0.2 mol) of N-methylpropargylamine in 20 ml methylene chloride was added dropwise to a stirred and cooled (below 15°C.) solution of 40.2 g (0.2 mol) bromoacetyl bromide and 16 g (0.2 mol) sodium bicarbonate in 250 ml methylene chloride. The reaction mixture was allowed to warm to about 25°C. and stirred for 2 hours. The reaction mixture was then filtered and evaporated under reduced pressure to give an oily residue. The residue was diluted with 150 ml ether to form a two-phase mixture consisting of an ether phase and a dark oil. The ether phase was separated, dried over magnesium sulfate, and evaporated to give 32.3 g of N-methyl-N-propargyl-α-bromoacetamide.

Workup

  1. stirringstirred for 2 hours
  2. filtrationThe reaction mixture was then filtered
  3. customevaporated under reduced pressure
  4. customto give an oily residue
  5. customto form a two-phase mixture
  6. customThe ether phase was separated
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-4e2ab9a786d7478fbf79ca559a0316c0
Source dataset
uspto-grants-1976_03
Patent number
US03944607

Reaction notes

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