Methylamine → N-methyl bromomaleimide

HRID 2224090Notes

Reaction equation

HRID 2224090 reaction equation
[Br:1][C:2]1[C:3](=O)[O:4][C:5](=[O:7])[CH:6]=1.[CH3:9][NH2:10].C(OC(=O)C)(=O)C>O.C(O)(=O)C>[Br:1][C:2]1[C:3](=[O:4])[N:10]([CH3:9])[C:5](=[O:7])[CH:6]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 7918Acetic AnhydrideHCID 800273-Bromo-2,5-furandione

Product 1

HCID 12136311N-methyl bromomaleimide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A 15 mmol solution of 3-bromo-2,5-furanedione and 15 mmol of methylamine at 40% in water, in 300 ml of glacial acetic acid is carried under reflux for 16 hours. After having allowed the reaction mixture to return to ambient temperature, 20 ml of acetic anhydride are added. The reaction medium is again brought to reflux under stirring for 4 hours before evaporating the solvents under reduced pressure. The expected product is obtained after purification by silica gel chromatography (heptane/ethyl acetate: 1/1) and recrystallization in ethanol.

Workup

  1. temperatureunder reflux for 16 hours
  2. customto return to ambient temperature
  3. temperatureto reflux
  4. custombefore evaporating the solvents under reduced pressure

Sources & evidence

ORD record
ord-d8e6c36cb7bb4b79b9185e452616b34a
Source dataset
uspto-grants-2008_05
Patent number
US07378419B2

Reaction notes

Loading…