反応 #95507

反応方程式

methanesulfonyl chloride

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

5-methyl-2-thienyl-α-hydroxybenzyl ketone

→

desired product

2,3,5,6,7,8-Hexahydro-3-(5-methyl-2-thienyl)-2-phenylthiazolo[3,2-a][1,3]diazepin-3-ol

溶媒

toluene

acetone

water

triethylamine

toluene

反応条件

後処理

1. 1
   workup.ADDITIONA mixture of 1.71 ml
2. 2
   その他the organic layer is separated
3. 3
   洗浄washed with water
4. 4
   濃縮concentrated to dryness
5. 5
   workup.ADDITIONportion of ether is added to the residue
6. 6
   その他giving a solid which
7. 7
   その他is collected
8. 8
   洗浄washed with ether
9. 9
   その他dried
10. 10
    その他giving 4.8 g
11. 11
    workup.ADDITIONA mixture of 2.01 g
12. 12
    workup.WAITto stand 48 hours
13. 13
    その他The solvent is removed
14. 14
    workup.ADDITIONof concentrated ammonium hydroxide are added
15. 15
    その他the resulting solid is collected
16. 16
    洗浄washed with water
17. 17
    workup.DISSOLUTIONThis solid is dissolved in 7 ml
18. 18
    温度of ethanol and then cooled
19. 19
    その他The resulting solid is collected
20. 20
    洗浄washed with ethanol
21. 21
    乾燥ether and dried in vacuo
22. 22
    その他giving 1.2 g

実験手順

A mixture of 1.71 ml. of methanesulfonyl chloride in 40 ml. of toluene is added dropwise to a stirred slurry of 4.65 g. of 5-methyl-2-thienyl-α-hydroxybenzyl ketone and 5.6 ml. of triethylamine in 40 ml. of toluene. The mixture is stirred 20 hours, water is added and the organic layer is separated, washed with water and concentrated to dryness. A 20 ml. portion of ether is added to the residue giving a solid which is collected, washed with ether and dried, giving 4.8 g. of 5-methyl-2-thienyl-α-hydroxybenzyl ketone methanesulfonate ester. A mixture of 2.01 g. of this ester and 0.84 g. of hexahydro-2H-1,3-diazepine-2-thione in 40 ml. of acetone is allowed to stand 48 hours. The solvent is removed, 50 ml. of water and one ml. of concentrated ammonium hydroxide are added and the resulting solid is collected and washed with water. This solid is dissolved in 7 ml. of ethanol and then cooled. The resulting solid is collected, washed with ethanol, then ether and dried in vacuo, giving 1.2 g. of the desired product as a yellow solid, m.p. 70°-90° C.

出典