Benzyl Bromide → N-ethyl-3-benzyloxy-4-nitrobenzamide

N-Ethyl-3-hydroxy-4-nitrobenzamide (5.23 g, 24.9 mmol) obtained in Example 312a) was dissolved in anhydrous DMF (100 ml), potassium carbonate (4.47 g, 32.3 mmol, 1.3 eq.) was added at room temperature, benzyl bromide (3.17 ml, 26.1 mmol, 1.05 eq.) was added dropwise, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with 5% aqueous sodium hydrogen carbonate solution (200 ml) and extracted with ethyl acetate-hexane (3:1, 200 ml and 150 ml). The organic layer was washed sequentially with 5% aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated, and diethyl ether was added to the residue. The precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a yellow powder (5.42 g, 18.1 mmol, 72.5%).

1. extractionextracted with ethyl acetate-hexane (3:1, 200 ml and 150 ml)
2. washThe organic layer was washed sequentially with 5% aqueous sodium hydrogen carbonate solution and saturated brine
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated
5. additiondiethyl ether was added to the residue
6. filtrationThe precipitate was collected by filtration
7. washwashed with diethyl ether
8. customdried

ORD-Eintrag

ord-8b57f31f9a6c4aedaf445edd95333ad9

Quelldatensatz

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07803822B2