Potassium Hydroxide → HCID 15453202, compound

HRID 378451Notes

Reaction equation

HRID 378451 reaction equation
[C:1]1([S:7]([N:10]([C:20]2[O:24][N:23]=[C:22]([CH3:25])[C:21]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)S(C2C=CC=CC=2)(=O)=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[OH-].[Na+]>CO>[CH3:25][C:22]1[C:21]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[C:20]([NH:10][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:8])=[O:9])[O:24][N:23]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 15453201HCID 15453201, compound

Product 1

HCID 15453202HCID 15453202, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

N-Benzenesulfonyl-N-(3-methyl-4-phenyl-5-isoxazolyl)benzenesulfonamide (300 mg, 0.66 mmol) was dissolved in methanol. Potassium hydroxide (300 mg, 5.5 mmol) was added and the solution was warmed to 45° C. to dissolve the sodium hydroxide. Stirring was continued for 20 min. Methanol was removed under reduced pressure. The residue was dissolved in water, cooled to 0° C. and acidified to pH 3-4 with concentrated HCl. The solid precipitate was extracted with ethyl acetate, dried and evaporated in vacuo to give 210 mg (100% yield) of N-(3-methyl-4-phenyl-5-isoxazolyl)benzenesulfonamide, which was further purified by recrystallization from ethyl acetate/hexanes, m.p. 124-126° C.

Workup

  1. customMethanol was removed under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. temperaturecooled to 0° C.
  4. extractionThe solid precipitate was extracted with ethyl acetate
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e4bf02eab21946eca988f936fa770bf7
Source dataset
uspto-grants-2000_02
Patent number
US06030991

Reaction notes

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