反応 #72569

反応方程式

triethylamine

Ethyl(methylsulphanyl)acetate

compound

3-(4-Amino-benzyl)-5-(4-chloro-phenyl)-3,6-dihydro-[1,3,4]oxadiazin-2-one

HCl

tBuOCl

→

title product

5-[5-(4-Chloro-phenyl)-2-oxo-6H-[1,3,4]oxadiazin-3-ylmethyl]-3-methyl-sulphanyl-1,3-dihydro-indol-2-one

溶媒

THF

反応条件

後処理

1. 1
   その他the temperature between −60° C. and −55° C
2. 2
   その他is brought to ambient temperature
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITis carried out for a further 2 hours
5. 5
   その他The organic phase is evaporated
6. 6
   抽出the aqueous suspension is extracted with DCM
7. 7
   洗浄washed with 2M HCl solution
8. 8
   乾燥with saturated NaCl solution, dried over sodium sulphate
9. 9
   ろ過filtered
10. 10
    その他evaporated to dryness
11. 11
    その他The residue is triturated in ethyl ether
12. 12
    ろ過filtered
13. 13
    その他dried in vacuo

実験手順

Ethyl(methylsulphanyl)acetate (27.31 mmoles) is added dropwise to a solution of the compound obtained in Step E (23.75 mmoles) in THF (200 ml) at −60° C. under a nitrogen atmosphere. tBuOCl (27.31 mmoles) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stirring for 3 hours at −60° C., triethylamine (29.68 mmoles) is added dropwise. The reaction mixture is brought to ambient temperature; aqueous 3M HCl solution (340 ml) is then added and stirring is carried out for a further 2 hours. The organic phase is evaporated and the aqueous suspension is extracted with DCM. The organic phases are combined, then washed with 2M HCl solution and then with saturated NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue is triturated in ethyl ether, filtered and dried in vacuo to yield the title product, which is used directly in the next Step.

出典