HCID 87203470, compound → HCID 66916070, compound

HRID 2061436Notes

Reaction equation

HRID 2061436 reaction equation
[CH2:1]([O:4][C:5]1[C:6]([S:18](=[O:25])(=[O:24])/[N:19]=C/N(C)C)=[C:7]([NH:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3]>C(O)C.Cl>[CH2:1]([O:4][C:5]1[C:6]([S:18](=[O:25])(=[O:24])[NH2:19])=[C:7]([NH:11][C:12](=[O:17])[C:13]([CH3:15])([CH3:16])[CH3:14])[CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 1

HCID 87203470HCID 87203470, compound

Product 1

HCID 66916070HCID 66916070, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

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 ammonia (pH 10 to 11) and EtOAc
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-8027f6d5e3fd4832847f3ce17645aba2
Source dataset
uspto-grants-2012_10
Patent number
US08283356B2

Reaction notes

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