m-Chloroperbenzoic acid → HCID 22151438, compound

HRID 703187Notes

Reaction equation

HRID 703187 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][S:10][C:11]2[NH:12][C:13]3[CH:19]=[C:18]4[O:20][CH2:21][O:22][C:17]4=[CH:16][C:14]=3[N:15]=2)[C:4]=1[CH3:23].ClC1C=CC=C(C(OO)=[O:32])C=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][S:10]([C:11]2[NH:15][C:14]3[CH:16]=[C:17]4[O:22][CH2:21][O:20][C:18]4=[CH:19][C:13]=3[N:12]=2)=[O:32])[C:4]=1[CH3:23]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22151440HCID 22151440, compound

Product 1

HCID 22151438HCID 22151438, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 330 mg of 6-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]-5H-1,3-dioxolo[4,5-f]benzimidazole in 5 ml of chloroform was treated portionwise with 200 mg of m-chloroperbenzoic acid while cooling with ice and stirring. After 15 minutes the reaction mixture was extracted with 10% sodium carbonate solution, dried and concentrated. The residue was chromatographed on silica gel with methylene chloride/methanol (8.5:1.5) as the elution agent, the medium pressure flash chromatography method being used and the pressure being produced with nitrogen. By recrystallization from ether there was obtained 6-[[(4-methoxy-3-methyl-2-pyridyl)methyl]sulfinyl]-5H-1,3-dioxolo[4,5-f]benzimidazole of melting point 185°-186° (decomposition).

Workup

  1. temperaturewhile cooling with ice
  2. extractionAfter 15 minutes the reaction mixture was extracted with 10% sodium carbonate solution
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel with methylene chloride/methanol (8.5:1.5) as the elution agent
  6. customthe pressure being produced with nitrogen
  7. customBy recrystallization from ether

Sources & evidence

ORD record
ord-2c6ed6ac5eea4bb292148c493b3d646d
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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