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

HRID 1030800

反応式

HRID 1030800 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.)

後処理

  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

出典と根拠

ORDレコード
ord-60405977b029430e9e592fcb8dafa81d
出典データセット
uspto-grants-1992_04
特許番号
US05106976

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