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

HRID 917566Notes

Reaction equation

HRID 917566 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[CH2:6]([NH:9][CH2:10][CH:11]=[CH2:12])[CH:7]=[CH2:8].CCN(CC)CC>C(OC(=O)C)C>[CH2:6]([N:9]([CH2:10][CH:11]=[CH2:12])[C:3](=[O:4])[CH2:2][Br:1])[CH:7]=[CH2:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31279DiallylamineHCID 61147Bromoacetyl bromide

Product 1

HCID 151934232-Bromo-N,N-di(prop-2-en-1-yl)acetamideYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Bromoacetyl bromide (45 g, 0.22 mol) in ethylacetate (25 mL) was added dropwise to a solution of diallyl amine (9.6 g, 0.1 mol), Et3N (15 mL), in ethyl acetate (50 mL) at 0° C. The reaction was then warmed to ambient temperature, and the stirring was continued for about 3 h. The resulting mixture was washed with saturated NaHCO3 solution (3×100 mL) and dried over Na2SO4. The evaporation of the solvent gave 16.2 g of product as a light yellow oil (yield 75%). ESI-MS (m/z): 218 (M+H+). 1H NMR δD (CDCl3): 5.75 (m, 2H, CH), 5.19 (m, 4H, CH2), 3.95 (d, 4H, NCH2), 3.81 (2, 2H, BrCH2).

Workup

  1. washThe resulting mixture was washed with saturated NaHCO3 solution (3×100 mL)
  2. dry with materialdried over Na2SO4
  3. customThe evaporation of the solvent

Sources & evidence

ORD record
ord-20976197d1b64cfebbf63ee05051531a
Source dataset
uspto-grants-2007_09
Patent number
US07273904B2

Reaction notes

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