반응 #323327

반응 방정식

thionyl chloride

sodium hydroxide

5-methoxy-2-[(1-methyl-3-pyrrolidinyl)oxy]-benzamide

triethylamine

hydrochloric acid

→

beige colored product

수율 23.2%

2-(2-Chloroethyl)-2,3-dihydro-7-methoxy-4-methyl-1,4-benzoxazepin-5(4H)-one

수율 23.2%

용매

water

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도at reflux for 24 hr
3. 3
   온도The reaction mixture was cooled
4. 4
   농축The mixture was concentrated under reduced pressure
5. 5
   여과The mixture was filtered
6. 6
   농축the filtrate was concentrated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in 500 ml of chloroform and to this solution
8. 8
   온도The mixture was heated
9. 9
   온도at reflux for 48 hr
10. 10
    온도cooled with an ice/acetone bath
11. 11
    기타did not exceed 25° C
12. 12
    세척The reaction solution was washed in sequence with water, 3N hydrochloric acid solution, water, 15% aqueous sodium hydroxide and water
13. 13
    건조finally dried over magnesium sulfate
14. 14
    기타The solvent was evaporated under reduced pressure
15. 15
    기타to give a black solid
16. 16
    기타The solid was purified on a silica gel column

실험 절차

To a solution of 19.2 g (0.48 mole) of sodium hydroxide in 500 ml of water was added 60 g (0.24 mole) of 5-methoxy-2-[(1-methyl-3-pyrrolidinyl)oxy]-benzamide and the mixture was heated at reflux for 24 hr. The reaction mixture was cooled and the pH adjusted to 6.8 with concentrated hydrochloric acid. The mixture was concentrated under reduced pressure and the residue was boiled in isopropyl alcohol for 1 hour. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in 500 ml of chloroform and to this solution was added 114 g (0.96 mole) of thionyl chloride. The mixture was heated at reflux for 48 hr, then cooled with an ice/acetone bath. To the mixture was added dropwise 97 g (0.96 mole) of triethylamine at such a rate that the temperature did not exceed 25° C. The reaction solution was washed in sequence with water, 3N hydrochloric acid solution, water, 15% aqueous sodium hydroxide and water and finally dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give a black solid. The solid was purified on a silica gel column using ethyl acetate as the eluting solvent to give on isolation 15 g (23%) of beige colored product, m.p. 98°-100° C.

출처