m-Chloroperbenzoic acid → 2-[2-(Isobutylamino)benzylsulfinyl]imidazo[4,5-b]pyridine

HRID 2107334

Reaktionsgleichung

Reaktionsgleichung von HRID 2107334
[CH2:1]([NH:5][C:6]1[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=1[CH2:8][S:9][C:10]1[NH:11][C:12]2[C:13]([N:18]=1)=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:2]([CH3:4])[CH3:3].ClC1C=CC=C(C(OO)=[O:31])C=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([NH:5][C:6]1[CH:22]=[CH:21][CH:20]=[CH:19][C:7]=1[CH2:8][S:9]([C:10]1[NH:11][C:12]2[C:13]([N:18]=1)=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:31])[CH:2]([CH3:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 148394372-[2-(Isobutylamino)benzylthio]imidazo[4,5-b]pyridine

Produkt 1

HCID 148394382-[2-(Isobutylamino)benzylsulfinyl]imidazo[4,5-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In 20 ml of chloroform was dissolved 900 mg of 2-[2-(isobutylamino)benzylthio]imidazo[4,5-b]pyridine. To the resulting solution was portionwise added under chilling with ice 618 mg of m-chloroperbenzoic acid (purity: 80%) over a period of 30 min. To the mixture was added a saturated NaHCO3 solution, and the resulting mixture was then stirred. The organic phase was separated and extracted successively with 20 ml of 0.1N NaOH and 10 ml of 0.1N NaOH. The alkaline extracts were combined and neutralized by NH4Cl, and the deposited oil was extracted with chloroform. The chloroform extract was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and placed under reduced pressure to distill off the solvent. The residue was crystallized by addition of diethyl ether. The crystalline product was washed with diethyl ether to give 195 mg of 2-[2-(isobutylamino)benzylsulfinyl]imidazo[4,5-b]pyridine as a pale yellow crystalline powder. m.p.: 116° C. (decompn.).

Aufarbeitung

  1. additionTo the resulting solution was portionwise added
  2. customThe organic phase was separated
  3. extractionextracted successively with 20 ml of 0.1N NaOH and 10 ml of 0.1N NaOH
  4. extractionthe deposited oil was extracted with chloroform
  5. extractionThe chloroform extract
  6. washwas washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. distillationto distill off the solvent
  9. customThe residue was crystallized by addition of diethyl ether
  10. washThe crystalline product was washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c3c599e2d6d74f9aaa00d14dd2451530
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04933458

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