Water → 6-bromo-1-methyl-1H-benzo(d)(1,3)oxazine-2,4-dione

5-bromoisatoic anhydride (3 g, 12 mmol) was stirred in 50 mL of DMF at 0° C. and sodium hydride (60% dispersion in mineral oil) (0.4 g, 15 mmol) was added in portions, with stirring for 1 hour at room temperature. Iodomethane (0.8 mL, 12 mmol) was added drop wise and the reaction mixture was allowed to stir for 4 hours. Water (50 mL) was added slowly and 50 mL of Dichloromethane (DCM) was also added. A white solid precipitated out and was filtered off. The layers were separated layers. Aqueous layer extracted with DCM (2×25 ml). The combined organic layers were extracted with water (4×25 ml) and once with brine (25 ml). The organic layer was dried with MgSO4 and the solvent removed. The residue was purified by flash chromatography (0-3% MeOH/DCM) to afford 1.57 g of product. Yield 49%

1. stirringto stir for 4 hours
2. customA white solid precipitated out and
3. filtrationwas filtered off
4. customThe layers were separated layers
5. extractionAqueous layer extracted with DCM (2×25 ml)
6. extractionThe combined organic layers were extracted with water (4×25 ml) and once with brine (25 ml)
7. dry with materialThe organic layer was dried with MgSO4
8. customthe solvent removed
9. customThe residue was purified by flash chromatography (0-3% MeOH/DCM)

ORDレコード

ord-f676b15974d04e83a9cc5e063e4e4b2a

出典データセット

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08017626B2