Ethyl Acetate → HCID 15233437, compound

HRID 1492734Notes

Reaction equation

HRID 1492734 reaction equation
[Cl-].[NH4+].[CH:3]1([O:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:11]=2[NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.C(OCC)(=O)C>[Fe].O>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][CH:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2)=[C:11]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:12]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 22406120HCID 22406120, compound

Product 1

HCID 15233437HCID 15233437, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To 100 ml of an aqueous solution containing 5.0 g of ammonium chloride were added 98.0 g of N-(2-cyclohexyloxy-5-nitrophenyl)methanesulfonamide and 78.0 g of an iron powder with heating at 80° C. with stirring, followed by stirring for 2 hours. The reaction solution was cooled back to room temperature, and then ethyl acetate and water were added thereto. After extraction, the organic layer was successively washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue was recrystallized from ethanol to give 71.7 g of N-(5-amino-2-cyclohexyloxyphenyl)methanesulfonamide as colorless prisms.

Workup

  1. stirringby stirring for 2 hours
  2. temperatureThe reaction solution was cooled back to room temperature
  3. extractionAfter extraction
  4. washthe organic layer was successively washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-b457087cf7b243f6800b3b0be175ae1d
Source dataset
uspto-grants-1994_12
Patent number
US05374764

Reaction notes

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