Dimethylformamide → HCID 178458205, compound

Participants

Reaction Steps

In a 50 ml capacity 3-neck round-bottomed flask attached with nitrogen bubbler, reflux condenser & magnetic stirrer methyl 2-isopropoxy-6-(trifluoromethyl)pyridine-4-carbimidothioate (5 g), formic hydrazide (0.431), dissolved in 50 ml DMF at RT for 20 min to form uncyclised form of 2-isopropoxy-4-(1H-1,2,4-triazol-3-yl)-6-(trifluoromethyl)pyridine which was confirmed by mass and on TLC as a polar spot as compared to starting material. Heated the reaction mixture at 80-90° C. for 6 h, which gave a non polar spot as compared to uncyclised form. The completion of the reaction was confirmed by TLC with 50% EtOAc-hexane as mobile phase. The reaction mixture was poured in ice water solution & extract with ethyl acetate (3×200 ml). Organic layer dried over Na2SO4 and concentrated to give crude product (5 g). The crude reaction mixture was purified by column chromatography using silica 60/120 using ethyl acetate:hexane as mobile phase. The column was packed in hexane and started eluting in ethyl acetate in gradient manner starting with fraction collection (25-mL fractions) from 5% to 25% ethyl acetate in hexane. Compound started eluting with 25% ethylacetate in hexane. Fraction containing such TLC profile was collected together to obtain pure 2-isopropoxy-4-(1H-1,2,4-triazol-3-yl)-6-(trifluoromethyl)pyridine (3.5 g).

Provenance & Evidence