反応 #72544

反応方程式

HCl

ethyl(methylsulphanyl)acetate

ethyl 4-amino-benzoate

tBuOCl

→

title product

Ethyl 3-methylsulphanyl-2-oxo-2,3-dihydro-1H-indole-5-carboxylate

溶媒

ether

triethylamine

DCM

反応条件

後処理

1. 1
   温度maintaining the temperature between −60° C. and −55° C
2. 2
   その他is brought to 0° C.
3. 3
   workup.STIRRINGAfter stirring for 12 hours at ambient temperature
4. 4
   その他the phases are separated
5. 5
   洗浄the organic phase is washed successively with aq. 2M HCl solution, water
6. 6
   乾燥The organic phase is dried over sodium sulphate
7. 7
   ろ過filtered
8. 8
   その他evaporated to dryness
9. 9
   その他The residue obtained
10. 10
    その他The crystals obtained
11. 11
    ろ過are filtered off
12. 12
    洗浄washed with ether
13. 13
    その他dried in vacuo

実験手順

To a solution of ethyl 4-amino-benzoate (40.0 g) in DCM (900 ml) at −60° C. there is added, dropwise, ethyl(methylsulphanyl)acetate (34.5 ml) under a nitrogen atmosphere. 29.0 g of tBuOCl are then added, dropwise, to the reaction mixture over 25 minutes, maintaining the temperature between −60° C. and −55° C. After stirring for one hour at −50° C., triethylamine (15.4 ml) is added dropwise. The reaction mixture is brought to 0° C. and then aqueous 3M HCl solution (485 ml) is added dropwise. After stirring for 12 hours at ambient temperature, the phases are separated and the organic phase is washed successively with aq. 2M HCl solution, water and then sat. aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The residue obtained is taken up in ether. The crystals obtained are filtered off, washed with ether and dried in vacuo to yield the title product, which is used directly in the next Step.

出典