반응 #4958

반응 방정식

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

수율 76.0%

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

수율 76.0%

용매

ethanol

반응 조건

후처리

1. 1
   온도the mixture heated to reflux
2. 2
   workup.DISSOLUTION(Complete dissolution occurred)
3. 3
   온도heating
4. 4
   온도heating
5. 5
   workup.WAITcontinued for 15 hr
6. 6
   온도at reflux
7. 7
   기타Solvent was removed by rotary evaporation (60° C., 30 mm Hg)
8. 8
   세척washed twice with dilute aqueous sodium hydroxide and once with water
9. 9
   건조The organic layer was dried over sodium sulfate
10. 10
    여과filtered
11. 11
    농축concentrated by rotary evaporation
12. 12
    기타azeotroped once with toluene
13. 13
    workup.ADDITIONThe oil was treated with oxalic acid in isopropyl alcohol which

실험 절차

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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