Hydrochloric Acid → HCID 501143, compound

HRID 2300978Notes

Reaction equation

HRID 2300978 reaction equation
C([NH:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:21])=[C:9]([CH:11]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=2[O-:20])[CH3:12])[CH:10]=1)(=O)C.OO.C([OH:26])C.Cl.[OH2:28]>CO>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH3:21])=[C:9]([CH:11]([S:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=2[O-:20])(=[O:26])=[O:28])[CH3:12])[CH:10]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 784Hydrogen Peroxide2×HCID 962Water3×HCID 18377459HCID 18377459, compound

Product 1

HCID 501143HCID 501143, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
39 °C

Procedure

To a stirred room temperature solution of 3.0 g (0.01 mole) of 2-[[1-(5-acetylamino-2-methylphenyl)ethyl]thio]-pyridine-N-oxide in 10 ml of methanol were added 0.12 g of Na2WO4 followed by 1 g of 35% hydrogen peroxide added over 20 minutes. The exothermic reaction was cooled using a room temperature water bath. The mixture was stirred for 20 minutes, and then treated dropwise with another 1.3 g of 35% H2O2. The mixture was warmed to 35-43° C. for two hours, and then left to stir at room temperature overnight. The mixture was then treated with 5 ml of ethanol, 10 ml of water, and 5 ml of concentrated HCl and heated on a steam cone for one hour. The mixture was cooled, diluted with 20 ml of water and filtered to remove a solid. The filtrate was made basic with concentrated aqueous ammonium hydroxide to give a tacky solid. This solid was taken up in 30 ml of water and 3 ml of concentrated HCl and some insoluble material was filtered off. The filtrate was basified to give a solid precipitate that was filtered off, washed with water, and left to dry overnight. The dry solid weighed 0.85 g and melted at 165-170° C. Recrystallization gave a solid with a melting point of 184-188° C. and having infrared and NMR spectra consistent with the proposed structure.

Workup

  1. additionadded over 20 minutes
  2. customThe exothermic reaction
  3. temperaturewas cooled
  4. customusing a room temperature
  5. waitleft
  6. stirringto stir at room temperature overnight
  7. temperatureheated on a steam cone for one hour
  8. temperatureThe mixture was cooled
  9. filtrationfiltered
  10. customto remove a solid
  11. customto give a tacky solid
  12. filtration3 ml of concentrated HCl and some insoluble material was filtered off
  13. customto give a solid precipitate that
  14. filtrationwas filtered off
  15. washwashed with water
  16. waitleft
  17. customto dry overnight
  18. customRecrystallization
  19. customgave a solid with a melting point of 184-188° C.

Sources & evidence

ORD record
ord-024a87c5ba724db6908d09d842ca2ddf
Source dataset
uspto-grants-2002_12
Patent number
US06498254B1

Reaction notes

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