Methanol → N-ethoxycarbonyl-2,3-dimethylmaleimide

HRID 921486Notes

Reaction equation

HRID 921486 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH3:7][C:8]1[C:9]([NH:11][C:12](=[O:15])[C:13]=1[CH3:14])=[O:10].C(N(CC)CC)C.CO>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:5]([O:4][C:2]([N:11]1[C:12](=[O:15])[C:13]([CH3:14])=[C:8]([CH3:7])[C:9]1=[O:10])=[O:3])[CH3:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 287932,3-Dimethylmaleimide

Product 1

HCID 23628596N-ethoxycarbonyl-2,3-dimethylmaleimideYield 80%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl chloroformate (1.5 ml, 15.6 mmol) was added dropwise to a stirred solution of 2,3-dimethylmaleimide (1.5 g, 12 mmol) and triethylamine (2 ml, 14 mmol) in dimethylformamide (10 ml) at 0-5° C. The reaction mixture was allowed to warm to room temperature and stand for 4 h. Methyl alcohol (10 ml) was added, diluted with chloroform (50 ml) and washed with water (3×20 ml). The chloroform solution was dried (Na2SO4) and concentrated in vacuum to give N-ethoxycarbonyl-2,3-dimethylmaleimide (yield 80%).

Workup

  1. washwashed with water (3×20 ml)
  2. dry with materialThe chloroform solution was dried (Na2SO4)
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-c9815ff0ad7f4f5e9e8fdb8fcb054b56
Source dataset
uspto-grants-2016_03
Patent number
US09273304B2

Reaction notes

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