2-Amino-5-methylbenzenesulfonamide → 2-[2-(4-Bromo-phenyl)-ethanesulfonylamino]-5-methyl-benzenesulfonamide

HRID 2283353Notes

Reaction equation

HRID 2283353 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][S:22](Cl)(=[O:24])=[O:23])=[CH:16][CH:15]=1>N1C=CC=CC=1.C(OCC)(=O)C>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][S:22]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=2[S:9]([NH2:12])(=[O:10])=[O:11])(=[O:24])=[O:23])=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 2455842-Amino-5-methylbenzenesulfonamideHCID 577510222-(4-Bromophenyl)ethane-1-sulfonyl chloride

Product 1

HCID 577509642-[2-(4-Bromo-phenyl)-ethanesulfonylamino]-5-methyl-benzenesulfonamideYield 38%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-amino-5-methyl-benzenesulfonamide (0.1 g, 0.53 mmol) and 2-(4-bromo-phenyl)-ethanesulfonyl chloride (0.14 g, 0.49 mmol) in anhydrous pyridine (4 mL) was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (20 mL) and the organic phase was washed with aqueous hydrochloric acid (1 M, 20 mL), saturated sodium bicarbonate (20 mL) and brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC, using 5% methanol in dichloromethane as the eluent, to give 80 mg (38% yield) of title compound.

Workup

  1. washthe organic phase was washed with aqueous hydrochloric acid (1 M, 20 mL), saturated sodium bicarbonate (20 mL) and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-98dc09cb8ff14154879c401123e1e025
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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