Reaktion #2385756

Reaktionsgleichung

methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate

1-(2H,3H-benzo[e]1,4-dioxin-6-yl)-2-bromoethan-1-one

→

methyl 4-[4-(3,4-ethylenedioxyphenyl)thiazol-2-yl]-5-methylthiothiophene-2-carboxylate

Ausbeute 95.1%

Lösungsmittel

acetone

—

reagent

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for 3 h
2. 2
   Temperaturto cool
3. 3
   Einengenwas concentrated in vacuo
4. 4
   workup.DISSOLUTIONThe crude product was dissolved in 50 mL of CH2Cl2
5. 5
   Sonstigepartitioned between 50 mL of 1 N NaOH (aq.)
6. 6
   SonstigeThe organic layer was obtained
7. 7
   Trocknendried over sodium sulfate
8. 8
   Einengenconcentrated

Vorschrift

40 mg (0.162 mmol) of methyl 4-(aminothioxomethyl)-5-methylthiothiophene-2-carboxylate (Maybridge Chemical Co. LTD., Cornwall, U.K.) was dissolved in 2 mL of reagent grade acetone. 1-(2H,3H-benzo[e]1,4-dioxin-6-yl)-2-bromoethan-1-one (0.162 mmol; 42 mg; Maybridge Chemical Co. LTD., Cornwall, U.K.) was added and the solution was allowed to reflux for 3 h. The solution was allowed to cool and allowed to stir for 2 days after which the reaction solution was concentrated in vacuo. The crude product was dissolved in 50 mL of CH2Cl2 and partitioned between 50 mL of 1 N NaOH (aq.). The organic layer was obtained and dried over sodium sulfate and concentrated to afford 60 mg (90% yield) of methyl 4-[4-(3,4-ethylenedioxyphenyl)thiazol-2-yl]-5-methylthiothiophene-2-carboxylate.

Quelle