Aniline → HCID 13150800, compound

HRID 2166588Notes

Reaction equation

HRID 2166588 reaction equation
[O:1]1[CH:6]([C:7]([OH:9])=[O:8])[CH:2]1[C:3]([OH:5])=O.[CH2:10]([K])[CH3:11].C(Cl)(=O)C(Cl)=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)C>[C:20]1([NH:19][C:3](=[O:5])[CH:2]2[O:1][CH:6]2[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 65578Oxalyl chlorideHCID 178461626HCID 178461626, compound

Product 1

HCID 13150800HCID 13150800, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of monoethyl potassium epoxysuccinate (1.7 g) in ethyl ether (30 ml), oxalyl chloride (1.2 g) in ethyl ether was added dropwise with stirring under ice-cooling and the mixture was stirred for an hour at room temperature. To the reaction mixture, aniline (1.6 g) in ethyl ether was added dropwise with stirring under ice-cooling, and the mixture was stirred at room temperature for an hour. The precipitate produced was filtered off and the filtrate was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated to dryness. The crude product was purified by chromatography using silica gel as an absorbent and benzene as an eluent, and then recrystallized from n-hexane-acetone to give 1.0 g of ethyl N-phenyl-2,3-epoxysuccinamate (Compound No. 1). m.p. 83°-84° C.

Workup

  1. additionwas added dropwise
  2. temperaturecooling
  3. stirringthe mixture was stirred for an hour at room temperature
  4. stirringwith stirring under ice-
  5. temperaturecooling
  6. stirringthe mixture was stirred at room temperature for an hour
  7. customThe precipitate produced
  8. filtrationwas filtered off
  9. washthe filtrate was washed with a saturated aqueous sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated to dryness
  12. customThe crude product was purified by chromatography
  13. customrecrystallized from n-hexane-acetone

Sources & evidence

ORD record
ord-9f4562ccf03f47e18096a063b708a9c7
Source dataset
uspto-grants-1983_06
Patent number
US04387238

Reaction notes

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