반응 #328925

반응 방정식

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

용매

THF

반응 조건

후처리

1. 1
   기타the temperature between −60° C. and −55° C
2. 2
   기타is brought to ambient temperature
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITis carried out for a further 2 hours
5. 5
   기타The organic phase is evaporated
6. 6
   추출the aqueous suspension is extracted with DCM
7. 7
   세척washed with 2M HCl solution
8. 8
   건조with saturated NaCl solution, dried over sodium sulphate
9. 9
   여과filtered
10. 10
    기타evaporated to dryness
11. 11
    기타The residue is triturated in ethyl ether
12. 12
    여과filtered
13. 13
    기타dried in vacuo

실험 절차

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.

출처