Dimethylformamide → 7-Bromo-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione

Temperatur

0 °C

Sodium hydride (0.47 g, 12 mmol) was added to a 3 neck 250 mL RBF under nitrogen and then washed with hexanes. Once the hexanes were decanted, N,N-dimethylformamide (20.0 mL, 11 mmol) was added. The resulting mixture was cooled to 0° C. using an ice-water bath, and then 7-bromo-1H-benzo[d][1,3]oxazine-2,4-dione (2.7 g, 11 mmol) was added in one batch. After stirring at room temperature for 1 hour, iodomethane (0.70 mL, 11 mmol) was added dropwise to the yellow solution, and the reaction mixture was stirred for 16 hours. Water (50 mL) was added, and the resulting precipitate that formed was collected via filtration. The solid was washed with additional water (100 mL), followed by ether (100 mL). Drying in a vacuum oven overnight at 50° C. afforded the desired product as an off-white solid (2.1 g, 74% yield).

1. washwashed with hexanes
2. customOnce the hexanes were decanted
3. stirringthe reaction mixture was stirred for 16 hours
4. customthe resulting precipitate that formed
5. filtrationwas collected via filtration
6. washThe solid was washed with additional water (100 mL)
7. customDrying in a vacuum oven overnight at 50° C.

ORD-Eintrag

ord-9063a8762dca471583d65bc743233cad

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08012968B2