Nitric Acid → HCID 18509206, compound

HRID 1356702Notes

Reaction equation

HRID 1356702 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[C:13]([CH3:18])=[N:14][O:15][C:16]=2[CH3:17])(=[O:11])=[O:10])=[CH:4][CH:3]=1.[N+:19]([O-])([OH:21])=[O:20].O>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][S:9]([C:12]2[C:13]([CH3:18])=[N:14][O:15][C:16]=2[CH3:17])(=[O:10])=[O:11])=[C:6]([N+:19]([O-:21])=[O:20])[CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 2741504HCID 2741504, compound

Product 1

HCID 18509206HCID 18509206, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of N-(4-Chlorophenyl)-3,5-dimethyl-4-isoxazolesulfonamide (1.10 g (3.84 mmol)) in acetic acid (4.0 ml), fuming nitric acid (0.20 ml (4.68 mmol)) was added dropwise with stirring at room temperature, and the mixture was heated at 50° C. for one hour with stirring. Water (20.0 ml) was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was washed with aqueous sodium hydroxide solution and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with acetone-chloroform-hexane(1:3:8) as eluent, to give 0.82 g (64%) of N-(4-chloro-2-nitrophenyl)-3,5 dimethyl-4-isoxazolesulfonamide as yellow crystals.

Workup

  1. temperaturethe mixture was heated at 50° C. for one hour
  2. stirringwith stirring
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with aqueous sodium hydroxide solution
  5. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-35365604ea7147d4b2bf735530841d55
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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