Reaktion #95510

Reaktionsgleichung

methanesulfonyl chloride

hexahydro-2H-1,3-diazepin-2-thione

4'-chloro-3,4-(methylenedioxy)benzoin

→

desired product

2-(p-Chlorophenyl)-2,3,5,6,7,8-hexahydro-3-[3,4-(methylenedioxy)phenyl]thiazolo[3,2-a][1,3]diazepin-3-ol hydrochloride

Lösungsmittel

toluene

triethylamine

acetone

acetone

toluene

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 1.55 ml
2. 2
   Sonstigethe organic layer is separated
3. 3
   Waschenwashed with water
4. 4
   Sonstigedried
5. 5
   Einengenrefrigerated and then concentrated to an oil
6. 6
   Sonstigegiving 8.3 g
7. 7
   workup.DISSOLUTIONThis oil is dissolved in 30 ml
8. 8
   workup.WAITto stand for 3 hours
9. 9
   Temperaturheated at 45°-50° C. for 3 hours, refrigerated overnight
10. 10
    Einengenconcentrated to about 1/3 its original volume
11. 11
    workup.ADDITIONAn equal volume of ether is added
12. 12
    Sonstigeproducing a gum
13. 13
    SonstigeThe solvent is removed
14. 14
    workup.ADDITIONof ammonium hydroxide are added
15. 15
    SonstigeThe solid is collected
16. 16
    Waschenwashed with water
17. 17
    Sonstigedried
18. 18
    workup.DISSOLUTIONdissolved in 25 ml
19. 19
    Filtrationfiltered and to the filtrate
20. 20
    workup.ADDITIONare added alcoholic hydrogen chloride and ether
21. 21
    FiltrationAfter refrigeration, the solid is filtered
22. 22
    Waschenwashed with ether
23. 23
    Filtrationof ethanol and filtered
24. 24
    workup.ADDITIONThe filtrate is treated with alcoholic hydrogen chloride
25. 25
    Temperaturcooled
26. 26
    Sonstigegiving 0.41 g

Vorschrift

A mixture of 1.55 ml. of methanesulfonyl chloride and 40 ml. of toluene is added over a period of one hour to a stirred mixture of 5.8 g. of 4'-chloro-3,4-(methylenedioxy)benzoin, 5.6 ml. of triethylamine and 20 ml. of toluene. The mixture is allowed to stand 4 hours, 50 ml. of water and more toluene are added, the organic layer is separated, washed with water, dried, refrigerated and then concentrated to an oil, giving 8.3 g. of the methanesulfonate ester. This oil is dissolved in 30 ml. of acetone and added to a stirred mixture of 1.95 g. of hexahydro-2H-1,3-diazepin-2-thione in 150 ml. of acetone. The mixture is allowed to stand for 3 hours, heated at 45°-50° C. for 3 hours, refrigerated overnight and concentrated to about 1/3 its original volume. An equal volume of ether is added producing a gum. The solvent is removed, 100 ml. of water and 2 ml. of ammonium hydroxide are added. The solid is collected, washed with water, dried and dissolved in 25 ml. of ethanol. This solution is refrigerated, then filtered and to the filtrate are added alcoholic hydrogen chloride and ether. After refrigeration, the solid is filtered, washed with ether, boiled with 25 ml. of ethanol and filtered. The filtrate is treated with alcoholic hydrogen chloride and cooled, giving 0.41 g. of the desired product, m.p. 184°-186° C.

Quelle