Peracetic Acid → HCID 501117, compound

HRID 2300983Notes

Reaction equation

HRID 2300983 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N+:12]=2[O-:17])=[O:10])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19].C(OO)(=[O:23])C>C(O)(=O)C>[N+:18]([C:3]1[CH:4]=[C:5]([CH2:8][S:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N+:12]=2[O-:17])(=[O:23])=[O:10])[CH:6]=[CH:7][C:2]=1[CH3:1])([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 6585Peracetic AcidHCID 18377465HCID 18377465, compound

Product 1

HCID 501117HCID 501117, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

To a mixture of 12.1 g (0.042 mole) 2-[[(4-methyl-3-nitrophenyl)methyl]sulfinyl]-pyridine-1-oxide in 35 ml of acetic acid was added, dropwise at room temperature over one-half hour, a solution of 9.2 g (1. 16 mole) of 40% peracetic acid in acetic acid. The reaction mixture was heated to 70° C. for two hours, and then allowed to cool and stir at room temperature overnight. An additional period of heating at 70° C. for five hours was instituted after which time work-up of a small portion of the mixture indicated some starting material to still be present. Heating and stirring at 70° C. for two more hours, and then standing at room temperature over the weekend completed the reaction. Excess peracetic acid was then destroyed with sodium bisulfite followed by the addition of 100 ml of water and neutralization with potassium carbonate. The aqueous mixture was chilled in an ice bath to precipitate yellow/white crystals. These were filtered off, washed with water and dried. Recrystallization from ethanol gave 2.9 g of white fluffy needles, having a melting point of 154-156° C. Infrared and NMR spectra were in agreement with the proposed structure.

Workup

  1. additionwas added, dropwise at room temperature over one-half hour
  2. temperatureto cool
  3. temperatureAn additional period of heating at 70° C. for five hours
  4. temperatureHeating
  5. stirringstirring at 70° C. for two more hours
  6. customstanding at room temperature over the weekend
  7. customthe reaction
  8. customExcess peracetic acid was then destroyed with sodium bisulfite
  9. additionfollowed by the addition of 100 ml of water and neutralization with potassium carbonate
  10. temperatureThe aqueous mixture was chilled in an ice bath
  11. customto precipitate yellow/white crystals
  12. filtrationThese were filtered off
  13. washwashed with water
  14. customdried
  15. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-ceca4974c1544ec4a18c1d15aa100f70
Source dataset
uspto-grants-2002_12
Patent number
US06498254B1

Reaction notes

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