4-Chloroaniline → HCID 2741504, compound

HRID 1356701Notes

Reaction equation

HRID 1356701 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1.[CH3:15][C:16]1[C:20]([S:21](Cl)(=[O:23])=[O:22])=[C:19]([CH3:25])[O:18][N:17]=1.C1OCCOCCOCCOCCOCCOC1>C(#N)C.O>[Cl:7][C:8]1[CH:14]=[CH:13][C:11]([NH:12][S:21]([C:20]2[C:16]([CH3:15])=[N:17][O:18][C:19]=2[CH3:25])(=[O:23])=[O:22])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 27363193,5-Dimethylisoxazole-4-sulfonyl chloride

Product 1

HCID 2741504HCID 2741504, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of potassium carbonate (0.18 g (1.28 mmol)) in acetonitrile (5.0 ml), 4-chloroaniline (0.33 g (2.56 mmol)), 3,5-dimethyl-4-isoxazolesulfonyl chloride (0.50 g (2.56 mmol)), 18-crown-6 (0.20 g (0.77 mmol)), were added with stirring at room temperature and the resulting mixture was stirred for 16 hours at the same temperature. Then, water (15.0 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 chloroform as eluent, to give 0.68 g (92%) of N-(4-chlorophenyl)-3,5-dimethyl-4-isoxazolesulfonamide.

Workup

  1. additionwere added
  2. stirringthe resulting mixture was stirred for 16 hours at the same temperature
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b69c6148abc24c8d94ce963644fbe16a
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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