HCID 87203470, compound → HCID 66916070, compound

HRID 2242041Notes

Reaction equation

HRID 2242041 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-(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-b10afd3799034ce0ba1ded14dcc7e04d
Source dataset
uspto-grants-2010_03
Patent number
US07671063B2

Reaction notes

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