Ethanol → HCID 22711205, compound

HRID 352916Notes

Reaction equation

HRID 352916 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][N+:32]([O-])=[C:31]([CH3:36])[CH:30]=4)=[CH:25][CH:24]=3)=[O:22])[CH2:17][CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[CH2:37]([OH:39])[CH3:38].ClCCl.C(=O)(O)[O-:44].[Na+]>C(OC(=O)C)(=O)C>[ClH:1].[C:37]([O:44][CH2:36][C:31]1[CH:30]=[C:29]([C:26]2[CH:25]=[CH:24][C:23]([C:21]([N:18]3[CH2:17][CH2:16][N:15]([S:12]([C:7]4[CH:6]=[CH:5][C:4]5[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=5)[CH:8]=4)(=[O:14])=[O:13])[CH2:20][CH2:19]3)=[O:22])=[CH:28][CH:27]=2)[CH:34]=[CH:33][N:32]=1)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 702EthanolHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 69700482HCID 69700482, compound

Product 1

HCID 22711205HCID 22711205, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

In acetic anhydride (25 ml), 4-[4-[[4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazin-1-yl]carbonyl]phenyl]-2-methylpyridine N-oxide (900 mg) was dissolved, followed by heating under reflux for 15 minutes. Ethanol (25 ml) was added to the reaction mixture and the resulting mixture was heated under reflux for further 1 hour. To the reaction mixture, dichloromethane and an aqueous solution of sodium bicarbonate were added to separate the organic layer. The organic layer thus obtained was dried over anhydrous sodium sulfate and 775 concentrated under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (dichloromethane˜1.5% methanol—dichloromethane), followed by crystallization from ethanol. The crystals were dissolved in dichloromethane and the resulting solution was made acidic by the addition of hydrochloric acid in ethanol. The resulting acidic mixture was concentrated, whereby the title compound (842 mg, 87%, pale yellow powder) was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 15 minutes
  3. temperaturethe resulting mixture was heated
  4. temperatureunder reflux for further 1 hour
  5. customto separate the organic layer
  6. customThe organic layer thus obtained
  7. dry with materialwas dried over anhydrous sodium sulfate and 775
  8. concentrationconcentrated under reduced pressure
  9. customto remove the solvent
  10. customThe residue was purified by chromatography on a silica gel column (dichloromethane˜1.5% methanol—dichloromethane)
  11. customfollowed by crystallization from ethanol
  12. dissolutionThe crystals were dissolved in dichloromethane
  13. additionthe resulting solution was made acidic by the addition of hydrochloric acid in ethanol
  14. concentrationThe resulting acidic mixture was concentrated

Sources & evidence

ORD record
ord-356d492f5fcf4ac6a22ad512d0ece783
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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