反応 #4958

反応方程式

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

収率 76.0%

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

収率 76.0%

溶媒

ethanol

反応条件

後処理

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
   その他Solvent was removed by rotary evaporation (60° C., 30 mm Hg)
8. 8
   洗浄washed twice with dilute aqueous sodium hydroxide and once with water
9. 9
   乾燥The organic layer was dried over sodium sulfate
10. 10
    ろ過filtered
11. 11
    濃縮concentrated by rotary evaporation
12. 12
    その他azeotroped once with toluene
13. 13
    workup.ADDITIONThe oil was treated with oxalic acid in isopropyl alcohol which

実験手順

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.

出典