Sodium Hydroxide → N-(4-bromo-3-tert-butyl-5-isoxazolyl)benzenesulfonamide

HRID 842884Notes

Reaction equation

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

Participants

Conditions

Temperature: 45 °C

Procedure

N-Benzenesulfonyl-N-(4-bromo-3-tert-butyl-5-isoxazolyl)benzenesulfonamide (80 mg, 0.16 mmol) was dissolved in methanol (2 ml). Sodium hydroxide (0.120 g, 3.0 mmol) in methanol was added and the solution was stirred at 45° C. 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 hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated in vacuo to give N-(4-bromo-3-tert-butyl-5-isoxazolyl)benzenesulfonamide in 94% yield. Further purification was achieved by recrystallization from methanol/water, giving an off white solid, m.p. 108-109° C.

Workup

customMethanol was removed under reduced pressure
dissolutionThe residue was dissolved in water
temperaturecooled to 0° C.
extractionextracted with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-507a05a21b9a46feb2973cffdae4b457
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376523B1

Reaction notes

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