反应详情

温度

130 °C

N-Methyl-4-nitro-benzamide (2.25 g, 12.5 mmol, 1 eq.) and PCl5 (2.60 g, 12.5 mmol, 1 eq.) were melted together under house vacuum connected to a NaOH trap behind a safety shield. Melting occurred at 100° C. Heated at 130° C. for 1 hour then purified by kugelrohr distillation at 0.1 mmHg at 130° C. CAUTION: THE EXPLOSIVE PROPERTIES OF THIS COMPOUND ARE UNKNOWN). The iminoyl chloride (12.5 mmol 1 eq.) in DMF 10 ml was added to NaN3 in 10 ml of DMF at 25° C. and stirred overnight. Worked up by adding EtOAc then rinsing 3× with H20. The organic layer was dried over MgSO4, then stripped to obtain yellow solids which were purified over silica gel in 3:1 hexanes/EtOAc to 100% EtOAc. Obtained 1.21 g of yellow solids as product. NMR (300 MHz, CDCl3) δ 8.46 (d, 2H, J=7 Hz), 8.02 (d, 2H, J=7 Hz),4.27 (s, 3H).

1. customconnected to a NaOH trap behind a safety shield
2. customoccurred at 100° C
3. distillationthen purified by kugelrohr distillation at 0.1 mmHg at 130° C
4. washthen rinsing 3× with H20
5. dry with materialThe organic layer was dried over MgSO4
6. customto obtain yellow solids which
7. customwere purified over silica gel in 3:1 hexanes/EtOAc to 100% EtOAc