反応 #95506

反応方程式

2'-chloro-3,4-dimethoxybenzoin

hexahydro-2H-1,3-diazepine-2-Thione

methanesulfonyl chloride

triethylamine

→

desired product

2-(o-Chlorophenyl)-3-(3,4-dimethoxyphenyl)-2,3,5,6,7,8-hexahydrothiazolo[3,2-a][1,3]diazepin-3-ol

溶媒

toluene

toluene

acetone

acetone

toluene

water

反応条件

後処理

1. 1
   workup.ADDITIONA mixture of 1.55 ml
2. 2
   その他The organic layer is separated
3. 3
   洗浄washed with water
4. 4
   濃縮concentrated in vacuo
5. 5
   その他to give 8.3 g
6. 6
   workup.ADDITIONA mixture of this oil in 30 ml
7. 7
   workup.STIRRINGThe resulting mixture is stirred for 3 hours
8. 8
   濃縮3 hours at 45°-50° C., concentrated to 1/3 of its original volume and ether
9. 9
   workup.ADDITIONis added
10. 10
    その他producing a gum
11. 11
    濃縮The mixture is concentrated free of solvents, 100 ml
12. 12
    workup.ADDITIONof ammonium hydroxide are added
13. 13
    ろ過the solid is filtered
14. 14
    洗浄washed with water
15. 15
    workup.DISSOLUTIONThis solid is dissolved in 20 ml
16. 16
    その他of ethanol and refrigerated giving 1.3 g

実験手順

A 6.13 g. portion of 2'-chloro-3,4-dimethoxybenzoin, 5.6 ml. of triethylamine and 20 ml. of toluene are mixed and stirred. A mixture of 1.55 ml. of methanesulfonyl chloride in 40 ml. of toluene is added over a period of one hour. A 50 ml. portion of water and more toluene are added. The organic layer is separated, washed with water and concentrated in vacuo to give 8.3 g. of 2'-chloro-3,4-dimethoxybenzoin methanesulfonate ester as a viscous oil. A mixture of this oil in 30 ml. of acetone is added to a stirred mixture of 1.95 g. of hexahydro-2H-1,3-diazepine-2-Thione in 150 ml. of acetone. The resulting mixture is stirred for 3 hours, then 3 hours at 45°-50° C., concentrated to 1/3 of its original volume and ether is added producing a gum. The mixture is concentrated free of solvents, 100 ml. of water and 2 ml. of ammonium hydroxide are added and the solid is filtered and washed with water. This solid is dissolved in 20 ml. of ethanol and refrigerated giving 1.3 g. of the desired product, m.p. 98°-100° C.

出典