Réaction #1150271

Équation de réaction

water

methanol

N-(4-Benzyloxy-7-morpholin-4-yl-benzothiazol-2-yl)-4-chloromethyl-benzamide

boron trichloride

→

title compound

Rendement 18.0%

4-Chloromethyl-N-(4-hydroxy-7-morpholin-4-yl-benzothiazol-2-yl)-benzamide

Rendement 18.0%

Solvants

CH2Cl2

CH2Cl2

Conditions de réaction

Traitement

1. 1
   TempératureAfter subsequent warming to 0°
2. 2
   Autrethe phases separated
3. 3
   ExtractionThe aqueous phases were extracted twice with CH2Cl2/MeOH
4. 4
   Séchagethe combined organic layers were dried with Na2SO4
5. 5
   Autreevaporated to dryness
6. 6
   AutreRecrystallization from CH2Cl2/MeOH

Mode opératoire

N-(4-Benzyloxy-7-morpholin-4-yl-benzothiazol-2-yl)-4-chloromethyl-benzamide (1.0 g, 2.0 mmol) were dissolved in CH2Cl2 (10 ml) and treated at −78° C. with tetrabutyl ammonium iodide (0.95 g, 2.6 mmol) and a solution of boron trichloride in CH2Cl2 (1M, 7.4 ml). After subsequent warming to 0° and stirring for additional 2 h, ice (2 g) and then water (10 ml) and methanol (2 ml) were added and the phases separated. The aqueous phases were extracted twice with CH2Cl2/MeOH, the combined organic layers were dried with Na2SO4 and evaporated to dryness. Recrystallization from CH2Cl2/MeOH afforded the title compound as an off-white solid (18%). MS: m/e=403 ([M−H+]−).

Source