반응 #4924

반응 방정식

fumaric acid

dimethylamine

ethanol

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

→

2-[2-(Dimethylamino)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-thione fumarate

용매

methanol

isopropyl alcohol

methylene chloride

isopropyl alcohol

반응 조건

후처리

1. 1
   기타The ethanol was removed in a rotary evaporator
2. 2
   기타leaving some water in the residue
3. 3
   세척washed with three 100 ml portions of 20% aqueous potassium carbonate solution
4. 4
   추출The combined aqueous layers were extracted with three 150 ml portions of methylene chloride
5. 5
   workup.ADDITIONtreated with charcoal
6. 6
   여과Charcoal was filtered off
7. 7
   기타the filtrate was evaporated
8. 8
   기타to give an oil
9. 9
   온도the solution was heated to a slow boil
10. 10
    기타Crystalline solid was obtained
11. 11
    기타The solid was recrystallized from hot 200 proof ethyl alcohol
12. 12
    여과The crystals were filtered off
13. 13
    기타triturated in isopropyl ether at room temperature
14. 14
    기타again separated
15. 15
    여과by filtering
16. 16
    기타After drying in a vacuum oven overnight at 85° C.
17. 17
    기타crystals in the amount of 72.45 g (79%), m.p. 130°-133° C., were obtained

실험 절차

To a solution of 113 ml (1.0 mole) of 40% aqueous dimethylamine and 326 ml of ethanol in a steel bomb was added 48.4 g (0.189 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-thione. The mixture was heated at 100° C. for 14 hr. The ethanol was removed in a rotary evaporator leaving some water in the residue. The residue was dissolved in 200 ml of methylene chloride and washed with three 100 ml portions of 20% aqueous potassium carbonate solution. The combined aqueous layers were extracted with three 150 ml portions of methylene chloride. Methylene chloride solutions were combined and treated with charcoal. Charcoal was filtered off and the filtrate was evaporated to give an oil. The oil was dissolved in 215 ml isopropyl alcohol and the solution was heated to a slow boil. A solution of 21.9 g (0.19 mole) of fumaric acid in 150 ml of boiling methanol was added to the isopropyl alcohol solution. Crystalline solid was obtained weighing 63.4 g (88%). The solid was recrystallized from hot 200 proof ethyl alcohol. The crystals were filtered off and triturated in isopropyl ether at room temperature and again separated by filtering. After drying in a vacuum oven overnight at 85° C., crystals in the amount of 72.45 g (79%), m.p. 130°-133° C., were obtained.

출처