Benzoyl chloride → N-(2-benzyloxy-5-chloro-4-nitrophenyl)benzamide

Beteiligte Stoffe

Reaktionsschritte

2-Benzyloxy-5-chloro-4-nitroaniline (31.63 g, 0.0828 mmol) was dissolved in 300 mL of dry methylene chloride in a dry 250 mL round bottom and sealed with a septum. Triethylamine (13.2 mL, 0.0947 mol, 1.1 equiv) was then added. Benzoyl chloride (31.1 mL, 0.268 mol, 3 equiv) was then added to dry methylene chloride (100 mL) in a self-equalizing dropping funnel and covered with a drying tube. The benzoyl chloride solution was added dropwise to the round bottom. The reaction mixture was allowed to stir for 15 minutes after addition of the benzoyl chloride solution. The solution was then refluxed overnight under a drying tube. The solution was diluted with chloroform (100 mL) and washed with 5% sodium bicarbonate (100 mL) and water (100 mL). The organic layer was dried with anhydrous sodium sulfate, gravity filtered and concentrated on a rotovap. Ethyl ether (150 mL) was added to the solid forming a suspension which was then suction filtered to yield N-(2-benzyloxy-5-chloro-4-nitrophenyl)benzamide as a peach solid (31.63 g, 0.0828 mol, 85%). Mp 158-160° C.; TLC (chloroform) Rf=0.62; 500 MHz 1H-NMR (CDCl3) 8.89 (s, 1H), 8.74 (s br, 1H), 7.80 (d, 8.0, 2H), 7.68 (s, 1H), 7.58 (t, 8.0, 1H), 7.48 (t, 8.0, 2H), 7.44 (m, 5H), 5.25 (s, 2H); IR (nujol) 3416, 3378, 1670, 1586, 1529, 1517, 1499, 1335, 1259, 1194. EI-MS m/z (relative intensity) 382 (M+, 7). Accurate mass for C20H15N2O4Cl: calcd. 382.0720, obsd. 382.0712.

Herkunft & Nachweise