Methanol → HCID 57524427, compound

Participants

Reaction Conditions

Reaction Steps

In a 3-neck 25 mL round-bottomed flask, (Z)-3-(3-(3-(methylsulfonyl)-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylohydrazide (0.300 g, 1.0 eq.) under N2 atmosphere was added trimethylorthoformate (0.26 g, 3.0 eq.) and Methane sulphonic acid (0.027 g, 0.1 eq.). Reaction mixture was refluxed at 80° C. for 1 h. The progress of the reaction was followed by TLC analysis on silica gel with 10% methanol: dichloromethane as mobile phase and visualization with UV, SM Rf=0.25 and Product Rf=0.41. The resulting yellow reaction mass was poured in 30 mL water and extracted with 3×20 mL ethylacetate. Organic layer was washed with brine solution followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 0.250 g of crude compound. The crude reaction mixture was purified by column chromatography using silica 60/120 using methanol: dichloromethane as mobile phase. The column (2×10 cm) was packed in dichloromethane and started eluting in Methanol in gradient manner starting with fraction collection (25-mL fractions) from 1.5% to 2.5% methanol in dichloromethane. Compound started eluting with 1.5% methanol in dichloromethane. Fraction containing such TLC profile was collected together to obtain pure compound (0.060 g), Yield (20%) 1H NMR (400 MHz, CDCl3) δ 9.76 (S, 1H), 7.2-8.6 (m, 7H), 7.39-7.41 (d, J=10.8, 1H), 5.58-5.88 (d, J=11.2 Hz, 1H), 5.39 (S, 2H), 4.70-4.73 (m, 1H), 1.39-1.41 (d, 6H): LCMS for C21H19F3N4O3 [M+1]+ 432.4 found 432.96 at RT 4.217 min.

Provenance & Evidence