Triethylamine → 5-(4-nitrophenyl)-3H-1,3-oxazol-2-one

HRID 56614

Reaction equation

HRID 56614 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:26])[CH2:18][N:19]2C(=O)CS[C:20]2=[O:25])=[CH:13][CH:12]=1)([O-:10])=[O:9]>C(O)C>[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:26][C:20](=[O:25])[NH:19][CH:18]=2)=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 115508943-[2-(4-Nitrophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione

Product 1

HCID 8221335-(4-nitrophenyl)-3H-1,3-oxazol-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.8 ml (20.1 mmol, 2.5 eq.) of triethylamine were added to a solution of 2.3 g (8.0 mmol) of 3-[2-(4-nitrophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione in 80 ml of ethanol, and the mixture was stirred under reflux for 14 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in water/ethyl acetate. After phase separation, the organic phase was dried (sodium sulphate), filtered, concentrated under reduced pressure and dried. The residue was stirred in dichloromethane and the precipitate was filtered off and dried under reduced pressure. Yield: 1.1 g (67% of theory)

Workup

  1. temperatureunder reflux for 14 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in water/ethyl acetate
  4. customAfter phase separation
  5. dry with materialthe organic phase was dried (sodium sulphate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customdried
  9. stirringThe residue was stirred in dichloromethane
  10. filtrationthe precipitate was filtered off
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-a47d7f766a624a55a6e6ffb16de5e965
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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