反応 #162362

反応方程式

water

ethyl 5-cyanotetrahydro-2H-1,2-oxazine-2-carboxylate

product

ethyl 5-cyanotetrahydro-2H-1,2-oxazine-2-carboxylate

thioacetamide

→

oil

ethyl 5-(aminothioxomethyl)tetrahydro-2H-1,2-oxazine-2-carboxylate

溶媒

trifluoroacetic acid

反応条件

後処理

1. 1
   抽出extracted with diethyl ether (3×10 mL)
2. 2
   洗浄The combined organic extracts were washed with water (10 mL)
3. 3
   乾燥dried over magnesium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated

実験手順

A mixture of ethyl 5-cyanotetrahydro-2H-1,2-oxazine-2-carboxylate (i.e. the product of Step H) (0.63 g, 0.0034 mol) and thioacetamide (0.72 g, 0.0096 mol) in trifluoroacetic acid (about 2 mL) was stirred at 50° C. for 20 h. The reaction mixture was poured into water (10 mL) and extracted with diethyl ether (3×10 mL). The combined organic extracts were washed with water (10 mL), dried over magnesium sulfate, filtered and concentrated to provide an orange oil (about 0.76 g). The resulting oil was adsorbed onto Celite® (diatomaceous filter aid), and then purified by silica gel column chromatography (25% to 50% gradient of ethyl acetate in petroleum ether as eluant) to provide the title compound (0.19 g).

出典