Potassium Hydroxide → N-(but-3-enyl)-2-nitro-N-phenylbenzenesulfonamide

HRID 62192Notes

Reaction equation

HRID 62192 reaction equation
[OH-].[K+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:14])=[O:13])([O-:5])=[O:4].Br[CH2:23][CH2:24][CH:25]=[CH2:26]>CN(C=O)C.CCOC(C)=O>[CH2:26]([N:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[S:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[N+:3]([O-:5])=[O:4])(=[O:14])=[O:13])[CH2:25][CH:24]=[CH2:23]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 21241Homoallyl bromideHCID 2296002-Nitro-N-phenylbenzenesulfonamide

Product 1

HCID 44131079N-(but-3-enyl)-2-nitro-N-phenylbenzenesulfonamideYield 64.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Crushed KOH (0.0484 g, 0.862 mmol, 1.2 equiv) was added to 2-nitro-N-phenylbenzenesulfonamide (0.200 g, 0.719 mmol) in 1 mL DMF, and the mixture was stirred for 30 min. 4-Bromo-1-butene (0.2426 g, 1.80 mmol) in 2 mL DMF solution was added dropwise into the mixture and it was stirred at room temperature overnight. The reaction mixture was diluted with 30 mL EtOAc and washed with 1M HCl2×10 mL and water 3×10 mL. The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using Hexanes/EtOAc to afford 0.1546 g white solid, yield 63.5%.

Workup

  1. stirringwas stirred at room temperature overnight
  2. washwashed with 1M HCl2×10 mL and water 3×10 mL
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customevaporated
  5. customto afford the crude product, which

Sources & evidence

ORD record
ord-4243304504ab41f6b0bc22c284bb5d5a
Source dataset
uspto-grants-2016_09
Patent number
US09446042B2

Reaction notes

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