Sodium hydride → HCID 14229165, compound

HRID 1073724Notes

Reaction equation

HRID 1073724 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH2:17].[H-].[Na+]>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]([CH3:13])[CH2:15][C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH2:17])(=[O:11])=[O:10])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 234998(3-bromoprop-1-en-2-yl)benzeneHCID 156724844-Cyano-N-methylbenzenesulfonamide

Product 1

HCID 14229165HCID 14229165, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2.30 g of 4-cyano-N-methylbenzenesulfonamide, 2.40 g of α-(bromomethyl)styrene and 20 ml of N,N-dimethylformamide, 0.63 g of 50% sodium hydride (oil dispersed) was slowly added with stirring under ice cooling, then the mixture was stirred at room temperature for 6 hours. After evaporating the solvent under a reduced pressure, ethyl acetate was added to the residue. The organic layer was washed with water and dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate n-hexane) to obtain 1.70 g of the titled compound.

Workup

  1. additionwas slowly added
  2. stirringthe mixture was stirred at room temperature for 6 hours
  3. customAfter evaporating the solvent under a reduced pressure, ethyl acetate
  4. additionwas added to the residue
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter distilling off the solvent
  8. customthe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate n-hexane)

Sources & evidence

ORD record
ord-4cf675f2292f473e8bef82312a2907b1
Source dataset
uspto-grants-1990_11
Patent number
US04971620

Reaction notes

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