반응 #47195

반응 방정식

KOH

methyl 5-tert-butyl-2-aminothiophene-3-carboxylate

methanol

→

6-tert-butyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dione

수율 96.0%

용매

H2O

반응 조건

후처리

1. 1
   기타The vial was capped
2. 2
   기타The solvent was removed under vacuum
3. 3
   workup.DISSOLUTIONthe crude product was dissolved in water (50 mL)
4. 4
   기타transferred to a 100 mL round bottom flask
5. 5
   workup.ADDITIONTo the vigorously stirred aqueous solution was added at room temperature drop wise phosgene (2M toluene, 6 mL) over a 15 minute period
6. 6
   workup.STIRRINGThe resulting mixture was stirred at room temperature overnight
7. 7
   기타The crude reaction mixture
8. 8
   여과was filtered
9. 9
   세척the precipitate was washed with water
10. 10
    기타dried
11. 11
    workup.DISSOLUTIONdissolved in ethyl acetate (10 mL)
12. 12
    건조The organic solution was dried over anhydrous sodium sulfate
13. 13
    여과filtered
14. 14
    기타the solvent was removed under vacuum

실험 절차

To a vial containing methyl 5-tert-butyl-2-aminothiophene-3-carboxylate (0.643 g) in 1:1 methanol: H2O (6 mL) was added KOH (0.5069 g). The vial was capped and the mixture was stirred at 80° C. for 6 h. The solvent was removed under vacuum and the crude product was dissolved in water (50 mL) and transferred to a 100 mL round bottom flask. To the vigorously stirred aqueous solution was added at room temperature drop wise phosgene (2M toluene, 6 mL) over a 15 minute period. The resulting mixture was stirred at room temperature overnight. The crude reaction mixture was filtered; the precipitate was washed with water, dried and dissolved in ethyl acetate (10 mL). The organic solution was dried over anhydrous sodium sulfate, filtered and the solvent was removed under vacuum to give 654.9 mg (96%) of the expected 6-tert-butyl-1H-thieno[2,3-d][1,3]oxazine-2,4-dione.

출처