2-(N-tert-butylsulfamoyl)-N-phenylacetamide → N-phenyl-2-sulfamoylacetamide

HRID 553467Notes

Reaction equation

HRID 553467 reaction equation
C([NH:5][S:6]([CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])(=[O:8])=[O:7])(C)(C)C>C(O)(C(F)(F)F)=O>[S:6]([CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])(=[O:7])(=[O:8])[NH2:5]

Participants

3

Reactant 1

HCID 579245132-(N-tert-butylsulfamoyl)-N-phenylacetamide

Product 1

HCID 21435949N-phenyl-2-sulfamoylacetamideYield 96.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The solution of compound 2-(N-tert-butylsulfamoyl)-N-phenylacetamide (2.5 g, 9.2 mmol.) in 40 mL of TFA was stirred at room temperature overnight. TLC analysis showed the reaction complete. Excess TFA was removed in vacuo. The value of pH was adjusted to 7-8 with NaHCO3. The mixture was extracted with EtOAc (30 mL×3). The combined organic layer was over Na2SO4, concentrated to afford compound 2-(sulfamoyl)-N-phenylacetamide (1.9 g, 96%), which was used directly without purification.

Workup

  1. customthe reaction complete
  2. customExcess TFA was removed in vacuo
  3. extractionThe mixture was extracted with EtOAc (30 mL×3)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f61b1478c836490cbcaeb3150c00e29a
Source dataset
uspto-grants-2011_11
Patent number
US08048862B2

Reaction notes

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