Methyl chloroformate → N-(Methoxycarbonyl)maleimide

HRID 383196

Reaction equation

HRID 383196 reaction equation
[CH3:1][O:2][C:3](Cl)=[O:4].[C:6]1(=[O:12])[NH:10][C:9](=[O:11])[CH:8]=[CH:7]1.CN1CCOCC1>CCOC(C)=O>[CH3:1][O:2][C:3]([N:10]1[C:6](=[O:12])[CH:7]=[CH:8][C:9]1=[O:11])=[O:4]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 10935Maleimide

Product 1

HCID 580610N-(Methoxycarbonyl)maleimideYield 55%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Methylchloroformate (4.4 mL, 56.7 mmol, 1 eq) was added to a solution of maleimide (5.5 g, 56.7 mmol, 1 eq) and NMM (6.2 mL, 56.7 mmol, 1 eq) in 200 mL of EtOAc at 0° C. The suspension was stirred at 0° C. for 30 minutes, filtered and washed with EtOAc. Filtrate and washings were combined and washed with cold water and dried over anhydrous Na2SO4. After filtration and evaporation under vacuum a pink solid was obtained. Purification by column chromatography on silica gel (Hexane-EtOAc, 1:1, v/v) provided the product (4.8 g, 55%).

Workup

  1. filtrationfiltered
  2. washwashed with EtOAc
  3. washwashed with cold water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationAfter filtration and evaporation under vacuum a pink solid
  6. customwas obtained
  7. customPurification by column chromatography on silica gel (Hexane-EtOAc, 1:1

Sources & evidence

ORD record
ord-f1acf67d1cd44f2980ceb3ef2322c62b
Source dataset
uspto-grants-2013_02
Patent number
US08367065B2

Linked notes

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