Methanol → ethyl 2,5-dioxopyrrole-1-carboxylate

HRID 921490Notes

Reaction equation

HRID 921490 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[C:7]1(=[O:13])[NH:11][C:10](=[O:12])[CH:9]=[CH:8]1.C(N(CC)CC)C.CO>CN(C)C=O.C(Cl)(Cl)Cl.CCCCCC>[CH2:5]([O:4][C:2]([N:11]1[C:7](=[O:13])[CH:8]=[CH:9][C:10]1=[O:12])=[O:3])[CH3:6]

Participants

8

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 10935Maleimide

Product 1

HCID 319934ethyl 2,5-dioxopyrrole-1-carboxylateYield 41%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

Ethyl chloroformate (0.38 ml, 4 mmol) was added dropwise to a stirred solution maleimide (0.3 g, 3 mmol) and triethylamine (0.5 ml, 3.5 mmol) in dimethylformamide (2 ml) at 0-5° C. The reaction mixture was allowed to warm to room temperature and stand for 4 h. Methyl alcohol (1 ml) was added, diluted with chloroform (20 ml) and washed with water (3×10 ml). The chloroform solution was dried (Na2SO4) and concentrated in vacuum. The residue was purified in chloroform and hexane on a silica gel column to give N-ethoxycarbonyl-maleimide (yield 41%).

Workup

  1. washwashed with water (3×10 ml)
  2. dry with materialThe chloroform solution was dried (Na2SO4)
  3. concentrationconcentrated in vacuum
  4. customThe residue was purified in chloroform

Sources & evidence

ORD record
ord-3ae2f3dd4c58410ab647411160b89d2a
Source dataset
uspto-grants-2016_03
Patent number
US09273304B2

Reaction notes

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