반응 #72562

반응 방정식

compound

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

sodium hydroxide

triethylamine

HCl

ethyl(methylsulphanyl)acetate

tBuOCl

→

title product

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

용매

CH3CN

THF

DCM

반응 조건

후처리

1. 1
   기타the temperature between −60° C. and −55° C
2. 2
   기타is brought to ambient temperature
3. 3
   workup.STIRRINGAfter stirring for 12 hours at ambient temperature
4. 4
   추출After extraction with DCM
5. 5
   세척the organic phase is washed with saturated aqueous NaCl solution
6. 6
   건조The organic phase is dried over sodium sulphate
7. 7
   여과filtered
8. 8
   기타evaporated to dryness
9. 9
   기타The product obtained
10. 10
    기타is triturated in ethyl ether
11. 11
    여과filtered
12. 12
    기타dried in vacuo

실험 절차

To a solution of the compound obtained in Step C (38.27 mmoles), in a mixture of CH3CN (115 ml) and THF (115 ml) at −60° C., ethyl(methylsulphanyl)acetate (45.92 mmoles) is added dropwise under a nitrogen atmosphere. tBuOCl (45.92 mmoles) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stirring for 1 hour at −60° C., triethylamine (51.66 mmoles) is added dropwise. The reaction mixture is brought to ambient temperature. 240 ml of DCM and then aqueous 3M HCl solution (340 ml) are added. After stirring for 12 hours at ambient temperature, the reaction mixture is made alkaline (pH 10-11) using 20% aqueous sodium hydroxide solution. After extraction with DCM, the organic phase is washed with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The product obtained is triturated in ethyl ether, filtered and dried in vacuo to yield the title product which is used directly in the next Step.

출처