Allyl bromide → HCID 87203470, compound

HRID 2061435Notes

Reaction equation

HRID 2061435 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. A solution of N-(3-allyloxy-2-{[1-dimethylamino-meth-(E)-ylidene]-sulfamoyl}-phenyl)-2,2-dimethyl-propionamide (387 mg, 1.05 mmol) in ethanol (12 ml) and 12 drops of conc HCl (aprox. 0.2 ml) is refluxed for 36 h. After evaporation of the solvent, the residue is partitioned between ammonia (pH 10 to 11) and EtOAc. The organic layer is dried (Na2SO4) and evaporated. Chromatography (silica gel, EtOAc/hexanes=2:1) afforded N-(3-allyloxy-2-sulfamoyl-phenyl)-2,2-dimethyl-propionamide containing some N-(3-allyloxy-2-sulfamoyl-phenyl)-2,2-dimethyl-propionamide. Treatment of this material with ethanol (20 ml) and conc. HCl (2 ml) for 30 h at reflux temperature and workup as above gives N-(3-allyloxy-2-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-5d473248b4824b7997f3d60d4239e1f1
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

Loading…