METHYL 3-(1H-1,2,4-TRIAZOL-1-YLMETHYL)BENZOATE synthesis

Yield:857284-24-3 71%

Reaction Conditions:

with potassium carbonate;potassium iodide in propan-2-one at 60; for 24 h;

Steps:

Methyl 3-((lH-l,2,4-triazol-l-yI)methyI)benzoate (TJA02008) C_{11H11N3O2 MW 217.22. Methyl 3-(bromobenzyl)benzoate (5.00 g, 21.8 mmol), 1,2,4-triazole (2.26 g, 32.7 mmol), potassium carbonate (3.01 g, 21.8 mmol), potassium iodide (0.213 g, 1.28 mmol) and acetone (100 mL) were loaded to an r.b. flask. With vigorous stirring this mixture was set to reflux (60 °C) for 24 h. The reaction mixture was allowed to cool and acetone was removed in vacuo. The residues were taken up in ethyl acetate (50 mL) and washed with distilled water (50 mL x 2) and brine (50 mL). Dried over MgSO4 and solvent removed in vacuo to leave a yellow oil. Column chromatography (ethyl acetate) eluted the title compound as a yellow viscous oil to give a yellow crystalline solid (3.35 g, 71 %), Rf 0.42 (ethyl acetate).¹H NMR (270 MHz, CDCl3) δ 3.86 (3H5 s, ArCO2CH3), 5.37 (2H5 s, ArCH2N)5 7.39- 7.44 (2H5 m5 ArH)5 7.93-7.94 (IH5 m, ArH), 7.96 (IH, s, C2H2N3), 7.97-8.01 (IH, m, ArH)5 and 8.09 (IH5 s, C2H2N3); ¹³C NMR (67.9 MHz5 CDCl3) δ 52.4 (CH3), 53.2 (CH2), 129.1 (CH), 129.3 (CH), 129.9 (CH), 131.1 (C)5 132.5 (CH)5 135.1 (C)5 143.2 (CH), 152.5 (CH) and 166.5 (C=O); HPLC (90 % CH3CN in H2O) tr=2.080 (100 %); LCMS (APCI), m/z 218.42 (M⁺ + H, 100 %).}

References:

WO2007/68905,2007,A1 Location in patent:Page/Page column 133-134