Reaktion #4450

Reaktionsgleichung

m-chloroperbenzoic acid

2-benzyl-4-(4-pyridyl)thiazole

m-chloroperbenzoic acid

→

4-[2-(phenylmethyl)-4-thiazolyl]pyridine-1-oxide

Ausbeute 95.0%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter an additional six hours of stirring the mixture
2. 2
   Extraktionwas extracted with saturated sodium bicarbonate (3×100 mL)
3. 3
   TrocknenThe organic layer was dried over sodium sulfate
4. 4
   Einengenconcentrated to a total volume of 75 mL

Vorschrift

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.

Quelle