Ethyl 5-methyl-1H-pyrazole-3-carboxylate → 5-methyl-1-phenylcarbamoyl-methyl-1H-pyrazole-3-carboxylic acid ethyl ester

Participants

Reaction Steps

To a magnetically stirred mixture of ethyl 5-methyl-1H-pyrazole-3-carboxylate (0.02 mol) and sodium ethoxide (0.22 mol) in ethanol (20 mL) is added the title A compound, 2-bromo-N-phenyl-acetamide (0.02 mol). The resulting suspension is stirred at RT for 3 h. After concentration in vacuo, EtOAc is added and the resulting solution is washed twice with water and dried over anhydrous Na2SO4. After filtration and concentration, the residue is purified by flash chromatography (ethyl acetate/hexane) to afford 5-methyl-1-phenylcarbamoyl-methyl-1H-pyrazole-3-carboxylic acid ethyl ester: m.p. 139-140° C.; 1H-NMR (DMSO-d6) δ 1.26-1.29 (t, 3H J=72 Hz), 2.28 (s, 3H), 4.23-4.25 (q, 2H J=72 Hz), δ 06 (s, 2H), δ 6.56 (s, 1H), 7.07 (m, 1H), 7.32 (m, 2H), 7.57 (m, 2H), 10.41 (s, 1H).

Provenance & Evidence