Methanol → HCID 57934778, compound

Temperature

80 °C

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.

1. customThe vial was capped
2. customThe solvent was removed under vacuum
3. dissolutionthe crude product was dissolved in water (50 mL)
4. customtransferred to a 100 mL round bottom flask
5. additionTo the vigorously stirred aqueous solution was added at room temperature drop wise phosgene (2M toluene, 6 mL) over a 15 minute period
6. stirringThe resulting mixture was stirred at room temperature overnight
7. customThe crude reaction mixture
8. filtrationwas filtered
9. washthe precipitate was washed with water
10. customdried
11. dissolutiondissolved in ethyl acetate (10 mL)
12. dry with materialThe organic solution was dried over anhydrous sodium sulfate
13. filtrationfiltered
14. customthe solvent was removed under vacuum

ORD record

ord-23bb3b7255a2406cb1eb3f414505a56f

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741479B2