Diallylamine → 2-Bromo-N,N-di(prop-2-en-1-yl)acetamide

HRID 1395703Notes

Reaction equation

HRID 1395703 reaction equation
[CH2:1]([NH:4][CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].C(=O)=O.CC(C)=O.[Br:15][CH2:16][C:17](Br)=[O:18]>C(Cl)Cl>[CH2:1]([N:4]([CH2:5][CH:6]=[CH2:7])[C:17](=[O:18])[CH2:16][Br:15])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 31279DiallylamineHCID 61147Bromoacetyl bromideHCID 18522661Acetone cardice

Product 1

HCID 151934232-Bromo-N,N-di(prop-2-en-1-yl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A 78-g (0.8 mol) sample of diallylamine was added dropwise to a stirred and cooled (dry-ice/acetone bath) solution of 80 g (0.4 mol) bromoacetylbromide in 200 ml methylene dichloride. The reaction mixture was allowed to warm to about 25° C. and stirred overnight. The reaction mixture was then washed with water, aqueous sodium bicarbonate, again with water, dried over magnesium sulfate and evaporated under reduced pressure to give 38 g N,N-diallyl-α-bromoacetamide.

Workup

  1. stirringstirred overnight
  2. washThe reaction mixture was then washed with water, aqueous sodium bicarbonate, again with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2659a5512d884c16bdeb31957abf27fd
Source dataset
uspto-grants-1980_05
Patent number
US04205168

Reaction notes

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