N-bromobutanimide → N-(4-bromo-3-methyl-5-isoxazolyl)-4-(3-methoxyphenyl)benzenesulfonamide

HRID 842874Notes

Reaction equation

HRID 842874 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[O:4][N:3]=1.C1C(=O)N([Br:32])C(=O)C1>>[Br:32][C:6]1[C:2]([CH3:1])=[N:3][O:4][C:5]=1[NH:7][S:8]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)=[CH:15][CH:16]=1)(=[O:10])=[O:9]

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 15453194N-(3-methyl-5-isoxazolyl)-4-(3-methoxyphenyl)benzenesulfonamide

Product 1

HCID 15453188N-(4-bromo-3-methyl-5-isoxazolyl)-4-(3-methoxyphenyl)benzenesulfonamide

Procedure

N-(4-bromo-3-methyl-5-isoxazolyl)-4-(3-methoxyphenyl)benzenesulfonamide was prepared in the same manner as described in Example 15 using N-(3-methyl-5-isoxazolyl)-4-(3-methoxyphenyl)benzenesulfonamide and NBS (reaction time 30 min at room temperature). The crude product was purified by column chromatography on silica gel using ethyl acetate as eluent giving the final product, after recrystallization using hexane/ethyl acetate, in 75% yield, m.p. 140-144° C.

Workup

  1. customN-(4-bromo-3-methyl-5-isoxazolyl)-4-(3-methoxyphenyl)benzenesulfonamide was prepared in the same manner
  2. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3cc93b33710e4e0db4d69914e89bb862
Source dataset
uspto-grants-2002_04
Patent number
US06376523B1

Reaction notes

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