Reaktion #472307

Reaktionsgleichung

2,3-dihydro-1,3-benzothiazole

2-aminobenzenethiol

formalin

diisopropylethylamine

3-formyl-4-methoxy-5-trifluoromethylbenzoyl chloride

→

title compound

3-(3-formyl-4-methoxy-5-trifluoromethylbenzoyl)-2,3-dihydro-1,3-benzothiazole

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure and water
2. 2
   workup.ADDITIONwas added
3. 3
   Extraktionthe mixture was extracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
7. 7
   Sonstigethe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Vorschrift

2,3-dihydro-1,3-benzothiazole synthesized from 2-aminobenzenethiol (1.55 g) and 37% formalin (1.0 mL) in the same manner as in Example 1 was dissolved in dichloromethane (15 mL), and diisopropylethylamine (2.7 mL) and 3-formyl-4-methoxy-5-trifluoromethylbenzoyl chloride (2.42 g) were added to the solution, and then the mixture was stirred at room temperature for 14 hours. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the title compound (1.44 g) as a yellow oily substance.

Quelle