Dimethyl Sulfoxide → 5-t-Butyl-2-(4-(2-hydroxyethylsulfonyl)-2-nitrophenyl)-4-iso-oxazolin-3-one

HRID 1649710Notes

Reaction equation

HRID 1649710 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][OH:13])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[C:17]([C:21]1[O:25][N:24]=[C:23]([OH:26])[CH:22]=1)([CH3:20])([CH3:19])[CH3:18].C(=O)(O)[O-].[Na+].CS(C)=O>O>[C:17]([C:21]1[O:25][N:24]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([CH2:11][CH2:12][OH:13])(=[O:10])=[O:9])=[CH:4][C:3]=2[N+:14]([O-:16])=[O:15])[C:23](=[O:26])[CH:22]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 136852842-(4-Chloro-3-nitrobenzenesulfonyl)ethanolHCID 178441207HCID 178441207, compound

Product 1

HCID 703746395-t-Butyl-2-(4-(2-hydroxyethylsulfonyl)-2-nitrophenyl)-4-iso-oxazolin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 g of 2-(4-chloro-3-nitrobenzenesulfonyl)ethanol, 19.1 g ot 5-t-butyl-3-hydroxyiso-oxazole, 28 g of sodium bicarbonate and 200 ml of dimethylsulfoxide were mixed together and reacted at 80° C. for a period of 8 hours. After cooling, the reaction mixture was poured into of water and the mixture was extracted with ethyl acetate. The organic layer was recovered and, after removing the solvent by distillation under reduced pressure, the main product was isolated using silica gel column chromatography as an oily product.

Workup

  1. customreacted at 80° C. for a period of 8 hours
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was recovered
  5. customafter removing the solvent
  6. distillationby distillation under reduced pressure
  7. customthe main product was isolated

Sources & evidence

ORD record
ord-c8ea836154d94960a58e5a8e9adf21c3
Source dataset
uspto-grants-1990_05
Patent number
US04921785

Reaction notes

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