Benzamide → 4'-Methylbenzanilide

Temperatur

140 °C

An oven-dried resealable Schlenk tube was charged with CuI (20 mg, 0.105 mmol, 5.1 mol %), benzamide (250 mg, 2.06 mmol), K2CO3 (600 mg, 4.34 mmol), evacuated and backfilled with argon. trans-1,2-Cyclohexanediamine (26 μL, 0.217 mmol, 10.5 mol %) and 4-chlorotoluene (1.0 mL, 8.44 mmol) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 140° C. for 46 h. The resulting black suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 2:1; 15 mL fractions). Fractions 5-15 were concentrated, the solid residue was suspended in 10 mL of hexane and filtered to provide 413 mg (95% yield) of the product as white crystals. The 1H NMR spectrum was in accord with that reported by Erdik et al. Erdik, E.; Daskapan, T. J. Chem. Soc., Perkin Trans. 1 1999, 3139.

1. customevacuated
2. customThe Schlenk tube was sealed
3. temperatureThe resulting black suspension was cooled to room temperature
4. filtrationfiltered through a 0.5×1 cm pad of silica gel eluting with 10 mL of ethyl acetate
5. concentrationThe filtrate was concentrated
6. customthe residue was purified by flash chromatography on silica gel (2×20 cm; hexane-ethyl acetate 2:1; 15 mL fractions)
7. concentrationFractions 5-15 were concentrated
8. filtrationfiltered

ORD-Eintrag

ord-6bd5e74e345a427e8a913259df154dd8

Quelldatensatz

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06759554B2