Sodium hydride → 2-Ethoxycarbonyl-2-(pyrrol-1-yl)-succinimide

HRID 256585Notes

Reaction equation

HRID 256585 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH2:16][C:17](=[O:19])[NH2:18])([N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[C:6](OCC)=[O:7])[CH3:2].[H-].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:5]1([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)[CH2:16][C:17](=[O:19])[NH:18][C:6]1=[O:7])=[O:20])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 106128722-Carbamoylmethyl-2-(pyrrol-1-yl)malonic acid diethyl ester

Product 1

HCID 108236892-Ethoxycarbonyl-2-(pyrrol-1-yl)-succinimideYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-carbamoylmethyl-2-(pyrrol-1-yl)malonic acid diethyl ester (29.0 g) in anhydrous dimethylformamide (30 ml) was added portionwise sodium hydride (63% dispersion in mineral oil, 4.3 g) under ice cooling. The resulting mixture was stirred under ice cooling for 1 hour, poured into 5% hydrochloric acid/ice-water, and extracted with ethyl acetate. The extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on silica gel using n-hexane/ethyl acetate (2:1) as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure to give the title compound (23.0 g, 94.7%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. additionFractions containing the title compound
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-238ff04c1658447e92fed48f069a68f3
Source dataset
uspto-grants-1993_11
Patent number
US05258382

Reaction notes

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