Réaction #302918

Équation de réaction

cyanuric chloride

3-hydroxymethylpyridothioxanthone

→

3-chloromethylpyridothioxanthone

Solvants

DCM

DMF

Dichloromethane

Conditions de réaction

Traitement

1. 1
   Autreresulting in a white precipitate
2. 2
   Lavagewashed with hydrochloric acid (0.5 M, 30 mL) and water
3. 3
   Séchagedried over sodium sulfate
4. 4
   AutreThe mixture was purified by column chromatography on silica gel with DCM/hexane (2:3) as the eluant

Mode opératoire

A solution of cyanuric chloride (0.29 g, 0.16 mmol) in DMF (1 mL) was stirred for 0.5 hrs, resulting in a white precipitate. Dichloromethane (30 mL) was added, followed by a solution of 3-hydroxymethylpyridothioxanthone (0.25 g, 1.0 mmol) in DCM (20 mL). The solution was stirred at r.t. overnight, then washed with hydrochloric acid (0.5 M, 30 mL) and water, and then dried over sodium sulfate. The mixture was purified by column chromatography on silica gel with DCM/hexane (2:3) as the eluant, yielding 3-chloromethylpyridothioxanthone (0.22 g, 82%). 1H-NMR (CDCl3): 8.88 (1H, d, J 8.4, H1), 8.61 (1H, d, J 8.1, H8), 7.73-7.64 (3H, m, H2+H5+H6), 7.57-7.52 (1H, m, H7), 4.76 (2H, s)). m/z (ES+): 262 [M+H]+, 284 [M+Na]+, 545 [2M+Na]+.

Source