반응 #1976490

반응 방정식

aniline

methyl 2-amino-5-ethylthiophene-3-carboxylate

triphosgene

triethylamine

→

title compound

수율 115.8%

6-ethyl-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

수율 115.8%

용매

methylene chloride

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was further stirred at room temperature for 1 hr
2. 2
   세척The reaction mixture was washed with water and saturated brine
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   기타The solvent was evaporated under reduced pressure
5. 5
   workup.DISSOLUTIONThe obtained residue was dissolved in methanol (20 mL)
6. 6
   workup.ADDITIONsodium methoxide (0.73 g) was added
7. 7
   workup.STIRRINGthe mixture was stirred at 60° C. for 2 hr
8. 8
   농축The reaction mixture was concentrated under reduced pressure
9. 9
   추출the obtained residue was extracted with 1N hydrochloric acid and ethyl acetate
10. 10
    세척The ethyl acetate layer was washed with saturated brine
11. 11
    건조dried over anhydrous magnesium sulfate
12. 12
    기타The solvent was evaporated under reduced pressure
13. 13
    여과The precipitated solid was collected by filtration

실험 절차

To a solution (40 mL) of methyl 2-amino-5-ethylthiophene-3-carboxylate (0.5 g) in methylene chloride were added triphosgene (0.32 g) and triethylamine (0.59 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added aniline (0.74 g), and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (20 mL), sodium methoxide (0.73 g) was added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was extracted with 1N hydrochloric acid and ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as a colorless solid (0.34 g, 46%).

출처