2-PHENYL-5-P-TOLYL-2H-PYRAZOL-3-YLAMINE synthesis

Yield:-

Reaction Conditions:

in dimethyl sulfoxide at 100; for 3 h;

Steps:

General procedure for the synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles

General procedure: To a 25 mL two-necked reaction flask, hydrazine (0.75 mmol), dimethylsulfoxide (DMSO) as solvent (1 mL) and benzoylacetonitrile (0.5 mmol) were added. This mixture was maintained for 3 hours under magnetic stirring at 100 °C. Then copper iodide (CuI) was added in the proportion of 20 mol% as catalyst, bipyridine (bpy) also in the proportion of 20 mol% as ligand and diaryl diselenide (0.5 mmol), where the reaction was maintained for a further 24 hours (when the substituents of the benzoylacetonitrile and hydrazine compounds varied, the reactions were maintained for 48 hours) under magnetic stirring at 100°C. After completion of the reaction, the mixture was poured into water (15 mL) and extracted with ethyl acetate (3 x 15 mL). Thereafter, the organic phase was dried with anhydrous magnesium sulfate (MgSO₄) and the solvent evaporated under vacuum. The product was purified from a silica gel chromatographic column, using a gravitational process using a hexane/ethyl acetate (96:4) mixture as eluent.

References:

Jacob, Raquel G.;Hartwig, Daniela;Nascimento, José Edmilson R.;Abib, Paola B.;Ebersol, Camila P.;Nunes, Pamela P.P.;Birmann, Paloma T.;Casaril, Angela M.;Savegnago, Lucielli;Schumacher, Ricardo F. [Tetrahedron Letters,2022,vol. 103,art. no. 153992] Location in patent:supporting information