Реакция #72562

Уравнение реакции

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

Растворители

CH3CN

THF

DCM

Условия реакции

Обработка

1. 1
   Другоеthe temperature between −60° C. and −55° C
2. 2
   Другоеis brought to ambient temperature
3. 3
   workup.STIRRINGAfter stirring for 12 hours at ambient temperature
4. 4
   ЭкстракцияAfter extraction with DCM
5. 5
   Промывкаthe organic phase is washed with saturated aqueous NaCl solution
6. 6
   СушкаThe organic phase is dried over sodium sulphate
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated to dryness
9. 9
   ДругоеThe product obtained
10. 10
    Другоеis triturated in ethyl ether
11. 11
    Фильтрацияfiltered
12. 12
    Другоеdried in vacuo

Методика

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.

Источник