Water → HCID 501121, compound

HRID 1829734Notes

Reaction equation

HRID 1829734 reaction equation
[Cl: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.S(=O)(=O)(O)[O-].[Na+].O>C(O)(=O)C>[Cl: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:23])=[O:10])=[CH:4][C:3]=1[N+:18]([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6585Peracetic AcidHCID 516919Sodium BisulfateHCID 22054754HCID 22054754, compound

Product 1

HCID 501121HCID 501121, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
70 °C

Procedure

To a mixture of 14.0 g (0.0426 mole) of 2-[[(4-chloro-3-nitrophenyl)methyl]sulfinyl]-pyridine-N-oxide in 35 ml of acetic acid was added 10.1 g of peracetic acid (40% in acetic acid) dropwise over one hour. The temperature of the reaction mixture rose to 27° C. before a water bath was placed on the flask to hold the temperature at 25° C. After addition, the mixture was heated to 70° C. for five hours. The mixture was cooled, and 20 ml additional acetic acid and solid sodium bisulfate and water were added to destroy the excess peracetic acid. The aqueous mixture was neutralized with potassium carbonate and chilled in an ice bath to precipitate an almost white solid. The precipitate was filtered off, washed with water, dried under vacuum overnight, and found to have a melting point of 162–164° C. Infrared and NMR spectra were both consistent with the proposed structure. The product was recrystallized from ethanol to give needle-like white crystals, melting point 168–170° C. C,H,N calculated for C12H9ClN2O5S: C=43.85%; H=2.76%; N=8.52%. Found: C=43.27%; H=2.65%; N=8.21%

Workup

  1. customThe temperature of the reaction mixture rose to 27° C. before a water bath
  2. customat 25° C
  3. additionAfter addition
  4. temperatureThe mixture was cooled
  5. customto destroy the excess peracetic acid
  6. temperaturechilled in an ice bath
  7. customto precipitate an almost white solid
  8. filtrationThe precipitate was filtered off
  9. washwashed with water
  10. customdried under vacuum overnight
  11. customThe product was recrystallized from ethanol
  12. customto give needle-like white crystals, melting point 168–170° C

Sources & evidence

ORD record
ord-848d9fae82004febad323d9dd83a5fe1
Source dataset
uspto-grants-2006_06
Patent number
US07064139B2

Reaction notes

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