Triethylamine → N-methyl bromomaleimide

HRID 929376Notes

Reaction equation

HRID 929376 reaction equation
[CH3:1][N:2]1[C:6](=[O:7])[CH:5]=[CH:4][C:3]1=[O:8].[Br:9]Br.C(N(CC)CC)C>CO>[CH3:1][N:2]1[C:6](=[O:7])[CH:5]=[C:4]([Br:9])[C:3]1=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24408BromineHCID 70261N-Methylmaleimide

Product 1

HCID 12136311N-methyl bromomaleimideYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To N-methyl maleimide (0.5 g, 4.5 mmol) in methanol (22.5 mL) was added bromine (0.52 mL, 10 mmol) dropwise. The reaction mixture was stirred at room temperature for 24 hours. Solvent was removed in vacuo and the reaction mass was dissolved in tetrahydrofuran (20 mL) and triethylamine (0.8 mL, 5.85 mmol) added, then stirred for 24 hours at room temperature. The material was purified by flash chromatography on silica gel (petroleum ether: ethyl acetate, 7:3) to afford a pale white powder (0.761 g, 4.0 mmol) in 89% yield.

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionthe reaction mass was dissolved in tetrahydrofuran (20 mL)
  3. stirringstirred for 24 hours at room temperature
  4. customThe material was purified by flash chromatography on silica gel (petroleum ether: ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-eb1a335b433d43a68a17646d669d21ae
Source dataset
uspto-grants-2016_03
Patent number
US09295729B2

Reaction notes

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