Nitric Acid → HCID 14771337, compound

HRID 476744Notes

Reaction equation

HRID 476744 reaction equation
[CH:1]1([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:20]([O-])([OH:22])=[O:21].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH:1]1([S:7][C:8]2[CH:13]=[C:12]([N+:20]([O-:22])=[O:21])[CH:11]=[CH:10][C:9]=2[NH:14][S:15]([CH2:18][CH3:19])(=[O:17])=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 14819602HCID 14819602, compound

Product 1

HCID 14771337HCID 14771337, compoundYield 63.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 20 ml of acetic acid was dissolved 1.5 g of N-[2-(cyclohexylthio)phenyl]ethanesulfonamide, 0.33 g of 61% nitric acid was added dropwise on heating at 80°-85° C., and then the mixture was stirred on heating for 1 hour. The reaction solution was poured into ice water, neutralized with a saturated sodium hydrogen carbonate solution and extracted with dichloromethane. The dichloromethane layer was washed, in turn, with a saturated aqueous sodium hydrogen carbonate solution, water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting crude crystals were purified by silica gel column chromatography (eluent: n-hexane:dichloromethane:ethyl acetate=20:10:1) and recrystallized from carbon tetrachloride-n-hexane to give 1.1 g of N-(2-cyclohexylthio-4-nitrophenyl)ethanesulfonamide.

Workup

  1. additionwas added dropwise
  2. temperatureon heating at 80°-85° C.
  3. temperatureon heating for 1 hour
  4. extractionextracted with dichloromethane
  5. washThe dichloromethane layer was washed, in turn, with a saturated aqueous sodium hydrogen carbonate solution, water
  6. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting crude crystals were purified by silica gel column chromatography (eluent: n-hexane:dichloromethane:ethyl acetate=20:10:1)
  9. customrecrystallized from carbon tetrachloride-n-hexane

Sources & evidence

ORD record
ord-cc279042210143b6bceb6758f6032388
Source dataset
uspto-grants-1989_12
Patent number
US04885367

Reaction notes

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