m-Chloroperbenzoic acid → HCID 14052185, compound

HRID 1030790Notes

Reaction equation

HRID 1030790 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:19]=[CH:18][CH:17]=[N:16][C:5]2=[N:6][C:7]=1[S:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.ClC1C=CC=C(C(OO)=[O:28])C=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[N:3]=[C:4]2[CH:19]=[CH:18][CH:17]=[N:16][C:5]2=[N:6][C:7]=1[S:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:28]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14052172HCID 14052172, compound

Product 1

HCID 14052185HCID 14052185, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 14 ml of chloroform was dissolved 1.4 g of 2-methyl-3-(2-pyridylmethylthio)pyrido[2,3-b]pyrazine. To the solution under chilling with ice was added portionwise 1.1 g of m-chloroperbenzoic acid (purity: 80%). The reaction mixture was then left to have room temperature, and poured into saturated aqueous NaHCO3 solution. The aqueous mixture was extracted with chloroform. The chloroform layer was washed with water and saturated aqueous sodium chloride solution, and dried over sodium sulfate. The sodium sulfate was then removed by filtration, and the solvent was evaporated under reduced pressure from the filtrate. The residue was purified by silica gel column chromatography (chloroform/methanol), to give 420 mg of 2-methyl-3-(2-pyridylmethylsulfinyl)-pyrido[2,3-b]pyrazine as a brown crystalline powder, m.p. 120°-125° C. (decompn.).

Workup

  1. temperatureTo the solution under chilling with ice
  2. waitThe reaction mixture was then left
  3. customto have room temperature
  4. extractionThe aqueous mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customThe sodium sulfate was then removed by filtration
  8. customthe solvent was evaporated under reduced pressure from the filtrate
  9. customThe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-2d2578c345dd41939901b3bf28e4bda9
Source dataset
uspto-grants-1992_04
Patent number
US05106976

Reaction notes

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