4-Toluenesulfonyl chloride → N-[5-bromo-3-hydroxypyridin-2-yl]-4-methylbenzenesulfonamide

HRID 14414Notes

Reaction equation

HRID 14414 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Br:12][C:13]1[CH:14]=[C:15]2[O:21]C(=O)[NH:19][C:16]2=[N:17][CH:18]=1.[OH-].[Na+]>>[Br:12][C:13]1[CH:14]=[C:15]([OH:21])[C:16]([NH:19][S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])=[N:17][CH:18]=1

Participants

4

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 136144586-Bromo-3H-oxazolo(4,5-b)pyridin-2-one

Product 1

HCID 23122883N-[5-bromo-3-hydroxypyridin-2-yl]-4-methylbenzenesulfonamide

Procedure

With 4-methylbenzenesulfonyl chloride, 6-bromo-[1,3]-oxazolo[4,5-b]pyridin-2(3H)-one (described in Heterocycles, 41, 2799 (1995)) was allowed to react. Then, with an aqueous solution of sodium hydroxide, the mixture was hydrolyzed to give the title compound having the following physical data.

Workup

  1. customto react

Sources & evidence

ORD record
ord-9538951dfb3948ce910f81244b76c00c
Source dataset
uspto-grants-2010_06
Patent number
US07732442B2

Reaction notes

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