Sodium Bicarbonate → 4-Hydroxy-N-(2-[1,2,3]triazol-1-yl-ethyl)-benzenesulfonamide

HRID 750974Notes

Reaction equation

HRID 750974 reaction equation
[N:1]1([CH2:6][CH2:7][NH2:8])[CH:5]=[CH:4][N:3]=[N:2]1.C(=O)([O-])O.[Na+].[OH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>C1COCC1>[OH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 114240934-Hydroxybenzene-1-sulfonyl chlorideHCID 225619722-(1H-1,2,3-Triazol-1-yl)ethanamine

Product 1

HCID 236145524-Hydroxy-N-(2-[1,2,3]triazol-1-yl-ethyl)-benzenesulfonamideYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 9.31 g (83.1 mmol) 2-[1,2,3]triazol-1-yl-ethylamine and 13.96 g (166 mmol) sodium hydrogencarbonate in 320 ml THF was added dropwise a solution of 16.0 g (83.1 mmol) 4-hydroxy-benzenesulfonylchloride in 160 ml THF at room temperature. Stirring was continued at 80° C. for 4 hours, then the solvent was evaporated and the residue triturated with 100 ml water to leave 16.05 g (72%) title compound as white solid melting at 220-223° C. (dec).

Workup

  1. customthe solvent was evaporated
  2. customthe residue triturated with 100 ml water

Sources & evidence

ORD record
ord-4c3694f13fd04a58ad8e60000b720706
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

Loading…