m-Chloroperbenzoic acid → 4-[2-(Phenylmethyl)-4-thiazolyl]pyridine-1-oxide

HRID 4354

Reaktionsgleichung

Reaktionsgleichung von HRID 4354
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([C:19]1[S:20][CH:21]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)[N:23]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[C:13]1([CH2:12][C:19]2[S:20][CH:21]=[C:22]([C:24]3[CH:25]=[CH:26][N+:27]([O-:9])=[CH:28][CH:29]=3)[N:23]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acid2×HCID 140969524-(2-Benzyl-1,3-thiazol-4-yl)pyridine

Produkt 1

HCID 142310544-[2-(Phenylmethyl)-4-thiazolyl]pyridine-1-oxideAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of m-chloroperbenzoic acid (14.5 g) in dry methylene chloride (150 mL) was added a solution of 2-benzyl-4-(4-pyridyl)thiazole (15.1 g, 0.06 mol) in methylene chloride (125 mL) over thirty minutes. The mixture was allowed to stir overnight at room temperature then an additional portion of m-chloroperbenzoic acid (3.00 g) was added. After an additional six hours of stirring the mixture was extracted with saturated sodium bicarbonate (3×100 mL). The organic layer was dried over sodium sulfate, and concentrated to a total volume of 75 mL. Dilution with ether (200 mL) afforded 4-[2-(phenylmethyl)-4-thiazolyl]pyridine-1-oxide (15.3 g, 95%). Recrystallization from ethanol/ether afforded an analytical sample. mp. 170°-172° C.

Aufarbeitung

  1. stirringAfter an additional six hours of stirring the mixture
  2. extractionwas extracted with saturated sodium bicarbonate (3×100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated to a total volume of 75 mL

Quellen und Nachweise

ORD-Eintrag
ord-c6e1cc3c94154c00aca4659516630175
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725606

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