Water → HCID 18509247, compound

HRID 1356703Notes

Reaction equation

HRID 1356703 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([C:14]2[C:15]([CH3:20])=[N:16][O:17][C:18]=2[CH3:19])(=[O:13])=[O:12])=[C:6]([N+:21]([O-:23])=[O:22])[CH:5]=1.S(OC)(O[CH3:28])(=O)=O.O>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH3:28])[S:11]([C:14]2[C:15]([CH3:20])=[N:16][O:17][C:18]=2[CH3:19])(=[O:13])=[O:12])=[C:6]([N+:21]([O-:23])=[O:22])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 18509206HCID 18509206, compound

Product 1

HCID 18509247HCID 18509247, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (65%, 0.05 g (1.36 mmol)) in DMF (3.0 ml), N-(4-chloro-2-nitrophenyl)-3,5-dimethyl-4-isoxazolesulfonamide (0.30 g (0.90 mmol)) was added with stirring at room temperature. To the mixture, after stirring for one hour at room temperature, dimethyl sulfate (0.13 ml (1.36 mmol)) was added dropwise, and the mixture was stirred for 16 hours. Water (20.0 ml) was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography with acetone-hexane (1:4) as eluent, to give 0.11 g (35%) of the title compound as white crystals.

Workup

  1. additionwas added
  2. stirringTo the mixture, after stirring for one hour at room temperature
  3. stirringthe mixture was stirred for 16 hours
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-64cefd436291481c9e527897707dafde
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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