反应 #4896

反应方程式

Hydrogen chloride

sodium 2-[(1-methyl-3-pyrrolidinyl)oxy]-3-pyridinecarboxylate

triphenylphosphine

carbon tetrachloride

→

2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one hydrochloride

溶剂

chloroform

ethanol

反应条件

后处理

1. 1
   温度at reflux for 1.5 hr
2. 2
   其他the heat removed
3. 3
   workup.STIRRINGThe solution was stirred for 1 hour
4. 4
   温度while cooling
5. 5
   workup.ADDITION200 ml of isooctane was added
6. 6
   萃取The solution was extracted 4 times with a total of 800 ml of dilute hydrochloric acid
7. 7
   萃取extracted with chloroform
8. 8
   其他The chloroform layer was separated
9. 9
   干燥dried over sodium sulfate
10. 10
    浓缩concentrated
11. 11
    workup.DISSOLUTIONThe residue was dissolved in a mixture of 500 ml each of isopropyl alcohol and isopropyl ether
12. 12
    其他A portion was recrystallized from isopropyl alcohol, m.p. 149°-153° C.

实验过程

Hydrogen chloride gas was bubbled into a suspension of 150 g (0.61 mole) of sodium 2-[(1-methyl-3-pyrrolidinyl)oxy]-3-pyridinecarboxylate in 1 liter of chloroform until a pH of 6 was reached. To the stirred mixture was added 350 g (1.34 mole) of triphenylphosphine and 350 g (2.3 mole) of carbon tetrachloride and the resulting cloudy solution was stirred at reflux for 1.5 hr. About 100 ml of ethanol was added and the heat removed. The solution was stirred for 1 hour while cooling and 200 ml of isooctane was added. The solution was extracted 4 times with a total of 800 ml of dilute hydrochloric acid. The acid extracts were combined, made basic with sodium hydroxide and extracted with chloroform. The chloroform layer was separated and dried over sodium sulfate and concentrated. The residue was dissolved in a mixture of 500 ml each of isopropyl alcohol and isopropyl ether and acidified with ethereal hydrogen chloride. The resulting crystals weighed 82 g (49%). A portion was recrystallized from isopropyl alcohol, m.p. 149°-153° C.

来源