반응 #4897

반응 방정식

thionyl chloride

hydrochloric acid

sodium hydroxide

4-chloro-2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide

→

dark-brown solid

수율 59.0%

8-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one

수율 59.0%

용매

ethyl acetate

water

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도at reflux for 24 hr
3. 3
   여과filtered
4. 4
   농축the filtrate concentrated
5. 5
   여과the mixture filtered
6. 6
   농축The filtrate was concentrated
7. 7
   온도heated
8. 8
   기타The excess thionyl chloride was evaporated under reduced pressure
9. 9
   workup.DISSOLUTIONThe residue was dissolved in 70 ml of chloroform
10. 10
    기타the solvent evaporated under reduced pressure
11. 11
    workup.DISSOLUTIONThe residue was redissolved in 75 ml of chloroform
12. 12
    workup.ADDITION40 ml of triethylamine was added gradually
13. 13
    온도The mixture was heated
14. 14
    온도at reflux for 1 hr
15. 15
    기타The solvent was evaporated under reduced pressure
16. 16
    기타to give a dark-brown solid
17. 17
    세척the resulting solution washed twice with 200 ml of water and twice with 250 ml of 20% sodium hydroxide
18. 18
    건조The organic layer was dried over magnesium sulfate
19. 19
    농축concentrated under reduced pressure

실험 절차

To a solution of 10.4 g (0.26 mole) of sodium hydroxide in 150 ml of water was added 32 g (0.13 mole) of 4-chloro-2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide and the mixture was heated at reflux for 24 hr. The reaction mixture was adjusted to pH 6 with concentrated hydrochloric acid and filtered and the filtrate concentrated. The residue was boiled with 100 ml of isopropyl alcohol and the mixture filtered. The filtrate was concentrated and heated at reflux with 98 g (b 0.83 mole) of thionyl chloride for 1 hr. The excess thionyl chloride was evaporated under reduced pressure. The residue was dissolved in 70 ml of chloroform and the solvent evaporated under reduced pressure. The residue was redissolved in 75 ml of chloroform and 40 ml of triethylamine was added gradually. The mixture was heated at reflux for 1 hr. The solvent was evaporated under reduced pressure to give a dark-brown solid. The solid was dissolved in ethyl acetate and the resulting solution washed twice with 200 ml of water and twice with 250 ml of 20% sodium hydroxide. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 21 g (59%) of dark-brown solid. The solid was recrystallized from isopropyl alcohol to give the title compound, m.p. 85°-87° C.

출처