Sulfuric Acid → HCID 13150876, compound

HRID 2166610Notes

Reaction equation

HRID 2166610 reaction equation
[C:1]1([NH:7][C:8](=[O:17])[CH:9]2[O:16][CH:10]2[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18](O)(C)C.S(=O)(=O)(O)O>C1C=CC=CC=1>[C:1]1([NH:7][C:8](=[O:17])[CH:9]2[O:16][CH:10]2[C:11]([O:13][CH:14]([CH3:18])[CH3:15])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 13150800HCID 13150800, compound

Product 1

HCID 13150876HCID 13150876, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of ethyl N-phenyl-2,3-epoxysuccinamate (Compound No. 1) (0.5 g) and isopropanol (1.0 g) in benzene (30 ml), a catalystic amount of a concentrated sulfuric acid was added, the mixture was refluxed for 5 hours. The reaction mixture was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated to dryness. The residue thus obtained was treated by silica gel column chromatography using benzene as a developer and the resulting crude crystals were recrystallized from a mixture of n-hexane-acetone to give 0.41 g of isopropyl N-phenyl-2,3-epoxysuccinamate (Compound No. 93) as colorless needles melting at 113°-114.5° C.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. washThe reaction mixture was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness
  5. customThe residue thus obtained
  6. additionwas treated by silica gel column chromatography
  7. customthe resulting crude crystals were recrystallized from a mixture of n-hexane-acetone

Sources & evidence

ORD record
ord-aedfb94fa4004b5d8b812b00cad5fea7
Source dataset
uspto-grants-1983_06
Patent number
US04387238

Reaction notes

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