反应 #302918

反应方程式

cyanuric chloride

3-hydroxymethylpyridothioxanthone

→

3-chloromethylpyridothioxanthone

溶剂

DCM

DMF

Dichloromethane

反应条件

后处理

1. 1
   其他resulting in a white precipitate
2. 2
   洗涤washed with hydrochloric acid (0.5 M, 30 mL) and water
3. 3
   干燥dried over sodium sulfate
4. 4
   其他The mixture was purified by column chromatography on silica gel with DCM/hexane (2:3) as the eluant

实验过程

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]+.

来源