Sodium Hydroxide → N-(4-Bromo-3-methyl-1,2-oxazol-5-yl)[1,1'-biphenyl]-4-sulfonamide

HRID 1167006Notes

Reaction equation

[C:1]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:6]=[CH:5][C:4]([S:7]([N:10]([C:26]2[O:30][N:29]=[C:28]([CH3:31])[C:27]=2[Br:32])S(C2C=CC(C3C=CC=CC=3)=CC=2)(=O)=O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH-].[Na+]>O1CCCC1>[Br:32][C:27]1[C:28]([CH3:31])=[N:29][O:30][C:26]=1[NH:10][S:7]([C:4]1[CH:3]=[CH:2][C:1]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:6][CH:5]=1)(=[O:8])=[O:9]

Participants

Conditions

Temperature: 45 °C

Procedure

N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide (0.150 g, 0.233 mmol) was dissolved in tetrahydrofuran (THF). Sodium hydroxide (0.120 g, 3.0 mmol) was added and the solution was warmed to 45° C. to dissolve the sodium hydroxide. Stirring was continued for 20 min. Tetrahydrofuran 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 filtered off and dried in vacuo to give N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide (94% yield), which was further purified by recrystallization from chloroform/hexanes, m.p. 133-135° C.

Workup

customTetrahydrofuran was removed under reduced pressure
dissolutionThe residue was dissolved in water
temperaturecooled to 0° C.
filtrationThe solid precipitate was filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-3a4cab8148ec4b9883a370832c0e4d95
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613804B2

Reaction notes

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