Triethylamine → Benzyl 2-(2,4-dinitrobenzamido)acetate

Beteiligte Stoffe

Reaktionsschritte

To a solution of benzyl glycinate.PTS salt (1.589 g, 4.716 mmol) in chloroform (20 mL) was added triethylamine (1.95 mL, 14. 148 mmol) at ice cold temperature. A solution of 2,4-dinitrobenzoyl chloride (prepared from 2,4-dinitrobenzoic acid, 1.0 g and SOCl2, 10 mL, refluxed for 2 h and evaporated the solvents) in chloroform (5 mL) was added to the above solution for 10 min and stirred for 1 h. After completion of the reaction, it was diluted with chloroform (100 mL). The chloroform layer was washed with water (2×50 mL), brine (50 mL) and dried over anhyd Na2SO4. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using chloroform:methanol (98:02) as eluents to give the product as an off-white color solid (1.55 g, 92%), mp 116-118° C. 1H NMR (400 MHz, CDCl3): δ 8.91 (1H, d, J=2.0 Hz), 8.52 (1H, dd, J=8.2, 2.2 Hz), 7.77 (1H, d, J=8.4 Hz), 7.38 (5H, s), 6.52-6.55 (1H, m), 5.24 (2H, s), 4.31 (2H, d, J=5.2 Hz); LC-MS (negative ion mode): m/z 358 (M−H)−.

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