m-Chloroperbenzoic acid → HCID 86753098, compound

HRID 2393507Notes

Reaction equation

HRID 2393507 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH:12]1[C:20]2[C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[S:17][C:16]=2[CH:15]=[C:14]([CH:25]([N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)[CH3:26])[CH:13]=1.C(=O)(O)[O-].[Na+].[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41]>C(Cl)(Cl)Cl.CC(C)=O>[C:37]([OH:44])(=[O:43])/[CH:38]=[CH:39]/[C:40]([OH:42])=[O:41].[N:27]1([CH:25]([C:14]2[CH:13]=[CH:12][C:20]3[C:19]4[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=4[S:17](=[O:9])[C:16]=3[CH:15]=2)[CH3:26])[CH:31]=[CH:30][N:29]=[CH:28]1

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 444972Fumaric AcidHCID 516892Sodium BicarbonateHCID 18976095HCID 18976095, compound

Product 1

HCID 86753098HCID 86753098, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

Under ice-cooling, m-chloroperbenzoic acid (0.18 g) was gradually added in small portions to a solution of 1-[1-(dibenzothiophen-3-yl) ethyl]-1H-imidazole (0.2 g) obtained in Example 8 in chloroform (5 ml), and the mixture was stirred at the same temperature for 2 hours. A saturated sodium bicarbonate aqueous solution was added and the chloroform layer was separated and dried over anhydrous magnesium sulfate. After evaporation of the solvent, the resulting residue was purified by silica gel column chromatography to obtain an oily material from a chloroform-methanol (100:1) eluate. This oily material was dissolved in acetone and mixed with 40 mg of fumaric acid which was dissolved by heating. After cooling, the thus precipitated crystals were washed with acetone to obtain 90 mg of 3-[1-(1H-imidazo1-1-yl)ethyl]dibenzothiophene-5-oxide monofumarate.

Workup

  1. temperatureUnder ice-cooling
  2. customthe chloroform layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter evaporation of the solvent
  5. customthe resulting residue was purified by silica gel column chromatography
  6. customto obtain an oily material from a chloroform-methanol (100:1) eluate
  7. dissolutionwas dissolved
  8. temperatureby heating
  9. temperatureAfter cooling
  10. washthe thus precipitated crystals were washed with acetone

Sources & evidence

ORD record
ord-97f896b473674543a61dc1ea1263c95d
Source dataset
uspto-grants-1998_09
Patent number
US05807880

Reaction notes

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