Sodium Hydroxide → HCID 18617352, compound

HRID 842891Notes

Reaction equation

HRID 842891 reaction equation
[OH-].[Na+].[C:3]1([S:9]([N:12]([C:22]2[C:26]([Br:27])=[C:25]([CH3:28])[O:24][N:23]=2)S(C2C=CC=CC=2)(=O)=O)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[Br:27][C:26]1[C:22]([NH:12][S:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)(=[O:11])=[O:10])=[N:23][O:24][C:25]=1[CH3:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18617325HCID 18617325, compound

Product 1

HCID 18617352HCID 18617352, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Sodium hydroxide (1.3 g, 30.6 mmol) was added to a solution of N-(benzenesulfonyl)-N-(4-bromo-5-methyl-3-isoxazolyl)benzene-sulfonamide (7g, 15.3 mmol, prepared as described in (a)) in methanol (100 ml). The resulting solution was stirred at 25° C. for 30 h. Excess methanol was removed under reduced pressure. The residue was dissolved in water (50 ml) and acidified (pH 3-4)by the addition of concentrated HCl with cooling. The mixture was extracted with dichloromethane (2×100 ml) and the combined organic layer was dried over anhydrous magnesium sulfate. Removal of the solvent gave N-(4-bromo-5-methyl-3-isoxazolyl)benzenesulfonamide which was purified by crystallization from ethyl acetate/hexanes (4.5 g, 92% yield). The compound is identical to the one isolated in step (b).

Workup

  1. customExcess methanol was removed under reduced pressure
  2. dissolutionThe residue was dissolved in water (50 ml)
  3. additionby the addition of concentrated HCl
  4. temperaturewith cooling
  5. extractionThe mixture was extracted with dichloromethane (2×100 ml)
  6. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-443981e63bb14d668959d6752695fc3e
Source dataset
uspto-grants-2002_04
Patent number
US06376523B1

Reaction notes

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