Aniline → HCID 21861134, compound

HRID 2166600Notes

Reaction equation

HRID 2166600 reaction equation
[O:1]1[CH:6]([C:7]([OH:9])=[O:8])[CH:2]1[C:3]([OH:5])=O.C[K].[C:12](Cl)(=O)C(Cl)=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCC)C>[C:19]1([NH:18][C:3](=[O:5])[CH:2]2[O:1][CH:6]2[C:7]([O:9][CH3:12])=[O:8])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 65578Oxalyl chlorideHCID 178524970HCID 178524970, compound

Product 1

HCID 21861134HCID 21861134, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of monomethyl potassium epoxysuccinate (1.0 g) in ethyl ether (30 ml), oxalyl chloride (0.75 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 (1.02 g) in ethyl ether was added dropwise with stirring under ice-cooling, and the mixture was stirred for an additional hour at room temperature. 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 to give 0.84 g of methyl N-phenyl-2,3-epoxysuccinamate (Compound No. 50) as colorless oil.

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 for an additional hour at room temperature
  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

Sources & evidence

ORD record
ord-32e12874da33403a80bd2c76b9af115d
Source dataset
uspto-grants-1983_06
Patent number
US04387238

Reaction notes

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