Allyl bromide → HCID 87203470, compound

HRID 2242040Notes

Reaction equation

HRID 2242040 reaction equation
[CH3:1][N:2]([CH3:22])/[CH:3]=[N:4]/[S:5]([C:8]1[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][C:9]=1[NH:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:7])=[O:6].[CH2:23](Br)[CH:24]=[CH2:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:25]([O:14][C:13]1[C:8]([S:5](=[O:7])(=[O:6])/[N:4]=[CH:3]/[N:2]([CH3:1])[CH3:22])=[C:9]([NH:15][C:16](=[O:21])[C:17]([CH3:19])([CH3:18])[CH3:20])[CH:10]=[CH:11][CH:12]=1)[CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 87203411HCID 87203411, compound

Product 1

HCID 87203470HCID 87203470, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(2-{[1-dimethylamino-meth-(E)-ylidene]-sulfamoyl}-3-hydroxy-phenyl)-2,2-dimethyl-propionamide (600 mg, 1.84 mmol) in DMF (4 ml) is treated at 70° C. with allyl bromide (217 μl, 2.57 mmol) and K2CO3 (380 mg) for 45 min with stirring. After evaporation of the solvent, the residue is partitioned between water and EtOAc. The organic layer is dried (Na2SO4) and evaporated yielding N-(3-allyloxy-2-{[1-dimethylamino-meth-(E)-ylidene]-sulfamoyl}-phenyl)-2,2-dimethyl-propionamide.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue is partitioned between water and EtOAc
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-b0bf463a3d5240be9907e49317113cc5
Source dataset
uspto-grants-2010_03
Patent number
US07671063B2

Reaction notes

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