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Triethylamine → 1-Propanol, 3-[[2-[(1H-benzimidazol-2-ylsulfinyl)methyl]-3-methyl-4-pyridinyl]oxy]-

HRID 727905
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 727905
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][S:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]=2)[C:7]=1[CH3:23].ClC1C=CC=C(C(OO)=[O:32])C=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][S:13]([C:14]2[NH:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)=[O:32])[C:7]=1[CH3:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 15166260Desmethyl rabeprazole thioether

Produkt 1

HCID 99061801-Propanol, 3-[[2-[(1H-benzimidazol-2-ylsulfinyl)methyl]-3-methyl-4-pyridinyl]oxy]-Ausbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

1.0 g (3.04 mmol) of 2-[{4-(3-hydroxypropoxy)-3-methylpyridine-2-yl}methylthio]-1H-benzimidazole was dissolved in 100 ml of dichloromethane to obtain a solution. 580 mg of 90% m-chloroperbenzoic acid was added to this solution at -45° C. The obtained mixture was stirred for 2 hours. After the completion of the reaction, 470 mg of triethylamine was added to the reaction mixture. The obtained mixture was heated to -20° C., followed by the addition of 30 ml of a saturated aqueous solution of sodium hydrogencarbonate. The obtained mixture was stirred at a room temperature for 30 minutes and extracted with chloroform. The obtained chloroform layer was concentrated to obtain a crude product. This crude product was crystallized from dichloromethane/ether to obtain 830 mg of 2-[{4-(3-hydroxypropoxy)-3-methylpyridine-2-yl}methylsulfinyl]-1H-benzimidazole. This product was dissolved in 24 ml of 0.1N aqueous sodium hydroxide. The obtained solution was distilled together with ethanol to remove the water as an azeotropic mixture with ethanol and dried under vacuumizing with a vacuum pump. Ether was added to the obtained residue to precipitate a colorless crystal. This crystal was separated by filtration. Thus, 860 mg of the title compound was obtained (77%).

Aufarbeitung

  1. customto obtain a solution
  2. additionwas added to the reaction mixture
  3. stirringThe obtained mixture was stirred at a room temperature for 30 minutes
  4. extractionextracted with chloroform
  5. concentrationThe obtained chloroform layer was concentrated
  6. customto obtain a crude product
  7. customThis crude product was crystallized from dichloromethane/ether

Quellen und Nachweise

ORD-Eintrag
ord-253457b8fedc48b99d03edbd54d3d254
Quelldatensatz
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05045552

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