Peracetic Acid → HCID 501116, compound

HRID 2300981Notes

Reaction equation

HRID 2300981 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:13][S:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N+:17]=2[O-:22])=[O:15])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-:3])=[O:2].C(OO)(=[O:25])C>C(O)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:13][S:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N+:17]=2[O-:22])(=[O:25])=[O:15])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6585Peracetic Acid2×HCID 18377461HCID 18377461, compound

Product 1

HCID 501116HCID 501116, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Conditions

Temperature
70 °C

Procedure

To 14.0 g (0.043 mole) of 2-[[(3,5-dinitrophenyl)methyl]sulfinyl]-pyridine-N-oxide in 35 ml of glacial acetic acid was added, dropwise over 0.5 hours with stirring, 8.2 g of 40% peracetic acid in acetic acid. After addition was complete, the mixture was heated to 70° C. for 4.5 hours. The mixture was cooled to room temperature, and then an additional 2.0 g of 40% peracetic acid was added, and the mixture heated to 45-50° C. for three hours while stirring. The mixture became quite thick, so 20 ml of glacial acetic acid was added to enable better stirring and heating was continued at 70° C. for one more hour, followed by stirring at 30° C. overnight. Workup of a small aliquot indicated some sulfoxide to still be present, so heating was continued at 65-70° C. for 4 more hours. The excess peracetic acid was then destroyed by adding 100 ml of water and sodium bisulfite. After neutralizing the mixture to pH 4 with potassium carbonate, the white solid was filtered off, and then dried under vacuum. Yield was 11.5 g or 79%, having a melting point of 198-201° C. This material was recrystallized from ethanol to give a white solid, melting point 202-204° C. Infrared and NMR spectra were consistent with the proposed structure.

Workup

  1. additionAfter addition
  2. temperatureThe mixture was cooled to room temperature
  3. temperaturethe mixture heated to 45-50° C. for three hours
  4. stirringwhile stirring
  5. stirringto enable better stirring
  6. temperatureheating
  7. customwas continued at 70° C. for one more hour
  8. stirringby stirring at 30° C. overnight
  9. temperatureso heating
  10. customwas continued at 65-70° C. for 4 more hours
  11. customThe excess peracetic acid was then destroyed
  12. additionby adding 100 ml of water and sodium bisulfite
  13. filtrationthe white solid was filtered off
  14. customdried under vacuum
  15. customThis material was recrystallized from ethanol
  16. customto give a white solid, melting point 202-204° C

Sources & evidence

ORD record
ord-43eb1eb294614984904be52d6a5fc156
Source dataset
uspto-grants-2002_12
Patent number
US06498254B1

Reaction notes

Loading…