反応 #61853

反応方程式

4-methyl-5-naphthalen-1-yl-oxazol-2-ylamine

N-chlorosuccinimide

→

4-chloromethyl-5-naphthalen-1-yl-oxazol-2-ylamine

収率 45.0%

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   温度at reflux for 8 hours
2. 2
   洗浄washed with a saturated solution of sodium hydrogen carbonate (50 mL), water (50 mL) and brine (50 mL)
3. 3
   その他The solvent was removed under reduced pressure
4. 4
   その他the resultant residue was purified by column chromatography

実験手順

A solution of 4-methyl-5-naphthalen-1-yl-oxazol-2-ylamine (3, 800 mg), N-chlorosuccinimide (480 mg) and dichloromethane (30 mL) were irradiated with a 150W (tungsten/halogen) lamp at reflux for 8 hours. After cooling to room temperature, the solution was diluted with dichloromethane (50 mL) and washed with a saturated solution of sodium hydrogen carbonate (50 mL), water (50 mL) and brine (50 mL). The solvent was removed under reduced pressure and the resultant residue was purified by column chromatography affording 4-chloromethyl-5-naphthalen-1-yl-oxazol-2-ylamine (27) (411 mg, 45%) as an orange foam, 1H NMR (DMSO-D6): 4.45 (2H, s), 6.95 (2H, br s), 7.5-7.6 (4H, m), 7.95-8.00 (3H, m).

出典