m-Chloroperbenzoic acid → HCID 9822781, compound

HRID 1736408Notes

Reaction equation

HRID 1736408 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[S:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]2.ClC1C=CC=C(C(OO)=[O:37])C=1>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[S:13]([CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]2)=[O:37]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10668289HCID 10668289, compound

Product 1

HCID 9822781HCID 9822781, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 1 liter of dichloromethane was dissolved 67 g of 6-{3-[1-(2-methylphenyl)-2-imidazolylthio]propoxy}-3,4-dihydrocarbostyril. Thereto was added 32.6 g of m-chloroperbenzoic acid with ice-cooling. The mixture was stirred overnight. After the completion of the reaction, the reaction mixture was washed five times with an aqueous solution saturated with sodium hydrogencarbonate, dried with magnesium sulfate, and subjected to distillation to remove the solvent. The residue was purified by a silica gel column chromatography (eluant: dichloromethane/ethyl acetate/methanol=30/10/1). The crude crystals were recrystallized from ethanol-n-hexane to obtain 39.5 g of 6-{3-[1-(2-methylphenyl)-2-imidazolylsulfinyl]propoxy}-3,4-dihydrocarbostyril.

Workup

  1. temperaturecooling
  2. customAfter the completion of the reaction
  3. washthe reaction mixture was washed five times with an aqueous solution saturated with sodium hydrogencarbonate
  4. dry with materialdried with magnesium sulfate
  5. distillationsubjected to distillation
  6. customto remove the solvent
  7. customThe residue was purified by a silica gel column chromatography (eluant: dichloromethane/ethyl acetate/methanol=30/10/1)
  8. customThe crude crystals were recrystallized from ethanol-n-hexane

Sources & evidence

ORD record
ord-a6a14bfac77f4b859839f5e9037b2ac6
Source dataset
uspto-grants-1996_07
Patent number
US05541198

Reaction notes

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