2-Nitrobenzenesulfonyl chloride → N-(Benzyloxy)-2-nitrobenzenesulfonamide

HRID 1424508Notes

Reaction equation

HRID 1424508 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].Cl.[CH2:15]([O:22][NH2:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH2:15]([O:22][NH:23][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 9839578N-(Benzyloxy)-2-nitrobenzenesulfonamideYield 69.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 2-nitrobenzene-1-sulfonyl chloride (500 g, 2.26 mol) in pyridine (1500 mL) was added dropwise to a 0° C. solution of O-benzylhydroxylamine hydrochloride (400 g, 2.51 mol) in pyridine (1500 mL). The reaction mixture was allowed to warm to room temperature then was stirred at 20° C. overnight. The mixture was concentrated under reduced pressure, diluted with DCM and washed with HCl (10%, 3×). The combined organic layer was concentrated under reduced pressure and re-crystallized with DCM to afford N-(benzyloxy)-2-nitrobenzenesulfonamide (485 g, 62.6%) as a yellow solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with DCM
  3. washwashed with HCl (10%, 3×)
  4. concentrationThe combined organic layer was concentrated under reduced pressure
  5. customre-crystallized with DCM

Sources & evidence

ORD record
ord-4f68dc4a4fa6487cb14d0d0aa7b554e2
Source dataset
uspto-grants-2015_01
Patent number
US08927724B2

Reaction notes

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