反应 #4958

反应方程式

ethylacetate methanol

diethylamine

diethylamine

diethylamine

ammonium hydroxide

7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-one

→

white crystals

收率 76.0%

7-Chloro-2-[2-(diethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one oxalate

收率 76.0%

溶剂

ethanol

反应条件

后处理

1. 1
   温度the mixture heated to reflux
2. 2
   workup.DISSOLUTION(Complete dissolution occurred)
3. 3
   温度heating
4. 4
   温度heating
5. 5
   workup.WAITcontinued for 15 hr
6. 6
   温度at reflux
7. 7
   其他Solvent was removed by rotary evaporation (60° C., 30 mm Hg)
8. 8
   洗涤washed twice with dilute aqueous sodium hydroxide and once with water
9. 9
   干燥The organic layer was dried over sodium sulfate
10. 10
    过滤filtered
11. 11
    浓缩concentrated by rotary evaporation
12. 12
    其他azeotroped once with toluene
13. 13
    workup.ADDITIONThe oil was treated with oxalic acid in isopropyl alcohol which

实验过程

To a suspension of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-one in 50 ml of absolute ethanol was added 2.26 ml (0.022 mole) of diethylamine and the mixture heated to reflux. (Complete dissolution occurred). After 1 hr, another 2.26 ml (0.022 mole) of diethylamine was added followed by 5.0 ml (0.049 mole) and heating continued for 2 more hours. TLC (ethylacetate/methanol/conc. ammonium hydroxide, 7:2:1, v/v/v) still showed presence of starting material; another 2.26 ml (0.022 mole) of diethylamine was added and heating continued for 15 hr at reflux. Solvent was removed by rotary evaporation (60° C., 30 mm Hg) and the residue taken up in methylene chloride, washed twice with dilute aqueous sodium hydroxide and once with water. The organic layer was dried over sodium sulfate, filtered and concentrated by rotary evaporation, and azeotroped once with toluene. The oil was treated with oxalic acid in isopropyl alcohol which yielded 6.7 g (76%) of white crystals, m.p. 163°-164° C.

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