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

HRID 1649524Notes

Reaction equation

HRID 1649524 reaction equation
[CH2:1]([O:8][NH2:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19](Cl)(=[O:21])=[O:20])([O-:12])=[O:11]>O1CCCC1>[C:2]1([CH2:1][O:8][NH:9][S:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N+:10]([O-:12])=[O:11])(=[O:20])=[O:21])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 102313O-Benzylhydroxylamine

Product 1

HCID 9839578N-(Benzyloxy)-2-nitrobenzenesulfonamideYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 96.4 g of O-benzylhydroxylamine in 80 ml of tetrahydrofuran was added to a solution of 86.8 g of o-nitrobenzenesulfonyl chloride in 400 ml of tetrahydrofuran at 5°-10°. After stirring at ambient temperature for 16 hours the solvent was evaporated. The residue was washed with water, filtered and dried to give 112.6 g of N-(phenylmethoxy)-2-nitrobenzenesulfonamide, m.p. 148°-151°.

Workup

  1. customwas evaporated
  2. washThe residue was washed with water
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-0eb95f8257334817bf38805635a23b9f
Source dataset
uspto-grants-1983_11
Patent number
US04417917

Reaction notes

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