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Toluene → 2-(((4-(5,9-dioxaspiro[3.5]non-7-yloxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1H-benzimidazole

HRID 31607
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 31607
C1(C)C=CC=CC=1.[CH2:8]1[C:11]2([O:16][CH2:15][CH:14]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][S:25][C:26]4[NH:30][C:29]5[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=5[N:27]=4)[C:19]=3[CH3:35])[CH2:13][O:12]2)[CH2:10][CH2:9]1.ClC1C=CC=C(C(OO)=[O:44])C=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.CO.CO>[CH2:10]1[C:11]2([O:16][CH2:15][CH:14]([O:17][C:18]3[CH:23]=[CH:22][N:21]=[C:20]([CH2:24][S:25]([C:26]4[NH:27][C:28]5[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=5[N:30]=4)=[O:44])[C:19]=3[CH3:35])[CH2:13][O:12]2)[CH2:8][CH2:9]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 597924692-(((4-(5,9-dioxaspiro[3.5]non-7-yloxy)-3-methylpyridin-2-yl)methyl)thio)-1H-benzimidazole

Produkt 1

HCID 120031212-(((4-(5,9-dioxaspiro[3.5]non-7-yloxy)-3-methylpyridin-2-yl)methyl)sulfinyl)-1H-benzimidazoleAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 21867641Toluene methanolLösungsmittel

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

To a toluene (30 ml)/methanol (3 ml) solution of the 2-(((4-(5,9-dioxaspiro[3.5]non-7-yloxy)-3-methylpyridin-2-yl)methyl)thio)-1H-benzimidazole (290 mg, 0.73 mmol) obtained in the step (9h), a toluene/methanol (10:1) solution of 3-chloroperbenzoic acid (174 mg, 0.65 mmol as the content was regarded as 65%) was added at −70° C. in a nitrogen atmosphere. After the mixture was stirred at −50° C. for one hour, a saturated aqueous solution of sodium hydrogen carbonate was added. After the mixture was warmed to room temperature, the mixture was extracted with ethyl acetate twice. Organic layers were combined and dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate, ethyl acetate/methanol=9/1). Fractions containing the title compound was collected by use of ethyl acetate and concentrated. After diethyl ether was added to the residue, the solvent was distilled off to obtain the title compound (230 mg, yield: 76.2%) as a white solid.

Aufarbeitung

  1. additionwas added at −70° C. in a nitrogen atmosphere
  2. temperatureAfter the mixture was warmed to room temperature
  3. extractionthe mixture was extracted with ethyl acetate twice
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate, ethyl acetate/methanol=9/1)
  8. additionFractions containing the title compound
  9. customwas collected by use of ethyl acetate
  10. concentrationconcentrated
  11. additionAfter diethyl ether was added to the residue
  12. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-9d7d5cdcaaa943238a9ce57c1f8a1516
Quelldatensatz
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07425634B2

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