Sodium Sulfite → HCID 18182256, compound

HRID 1359274Notes

Reaction equation

HRID 1359274 reaction equation
[C:1]([C:9]1[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=[C:11]([CH3:23])[N:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:32])C=1.S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[OH:32][CH2:23][C:11]1[N:10]=[C:9]([C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 18182278HCID 18182278, compound

Product 1

HCID 18182256HCID 18182256, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

113 g of 2-benzoyl-3-benzyloxy-6-methylpyridine was dissolved in 600 ml of dichloromethane. 96 g of 3-chloroperbenzoic acid was added thereto, followed by stirring under heating at 50° C. in an oil bath. After cooling in a water bath, an aqueous sodium sulfite solution and further an aqueous saturated sodium bicarbonate solution were added to the reaction solution. The organic phase was separated, further washed with an aqueous saturated sodium bicarbonate solution and brine. Then, it was dried over anhydrous magnesium sulfate and the solvent was removed. The resulting residue was dissolved in 200 ml of acetic acid anhydride, followed by heating under stirring at 150° C. for 3 hours in an oil bath. Then, the solvent was removed and 400 ml of methanol and 200 ml of an aqueous 2N sodium hydroxide solution were further added thereto, followed by heating under stirring at 60° C. for 3 hours in an oil bath. Activated carbon was added to the reaction solution. After stirring for a while, it was filtered off. Water was added to the filtrate to precipitate crystals. The resulting crystals were collected by filtration and vacuum-dried, to give 116 g of the target compound.

Workup

  1. temperatureAfter cooling in a water bath
  2. customThe organic phase was separated
  3. washfurther washed with an aqueous saturated sodium bicarbonate solution and brine
  4. dry with materialThen, it was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed
  6. dissolutionThe resulting residue was dissolved in 200 ml of acetic acid anhydride
  7. temperatureby heating
  8. stirringunder stirring at 150° C. for 3 hours in an oil bath
  9. customThen, the solvent was removed
  10. addition400 ml of methanol and 200 ml of an aqueous 2N sodium hydroxide solution were further added
  11. temperatureby heating
  12. stirringunder stirring at 60° C. for 3 hours in an oil bath
  13. additionActivated carbon was added to the reaction solution
  14. stirringAfter stirring for a while, it
  15. filtrationwas filtered off
  16. additionWater was added to the filtrate
  17. customto precipitate crystals
  18. filtrationThe resulting crystals were collected by filtration
  19. customvacuum-dried

Sources & evidence

ORD record
ord-ca73ad46c164445eba5f46d7891c549e
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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