Potassium Carbonate → 2-(2-sulfamoylphenoxy)-N-methylacetamide

HRID 553472

Reaction equation

HRID 553472 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](=[O:11])(=[O:10])[NH2:9].Br[CH2:13][C:14]([NH:16][CH3:17])=[O:15].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][CH2:13][C:14]([NH:16][CH3:17])=[O:15])(=[O:11])(=[O:10])[NH2:9]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6375462-Hydroxybenzene-1-sulfonamideHCID 154907452-Bromo-N-methylacetamide

Product 1

HCID 579243292-(2-sulfamoylphenoxy)-N-methylacetamideYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of crude 1-(hydroxy)-2-sulfamoylbenzene (400 mg, 2.4 mmol.) in 60 mL of acetonitrile was added 2-bromo-N-methylacetamide (332 mg, 2.4 mmol.), K2CO3 (662 mg, 4.8 mmol.) and KI (400 mg, 2.4 mmol.). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was filtered, concentrated and purified by prep-TLC to afford 2-(2-sulfamoylphenoxy)-N-methylacetamide (260 mg, 47%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified by prep-TLC

Sources & evidence

ORD record
ord-8bf3976ec43b4f69905ede8089b4f8b6
Source dataset
uspto-grants-2011_11
Patent number
US08048862B2

Linked notes

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