Methanesulfonic Acid → HCID 57524353, compound

Participants

Reaction Conditions

Reaction Steps

In a 25-mL, 3N round-bottomed flask equipped with nitrogen inlet, and a rubber septum, (Z)-3-(3-(3-chloro-5-isopropoxyphenyl)-1H-1,2,4-triazol-1-yl)acrylohydrazide (0.3 g, 1.0 eq.) was dissolved in THF (7.5 mL, 25V) and trimethylorthoformate (0.109 g, 1.1 eq) and added Methanesulphonic acid (0.053 g, 0.5 eq) was added into it. The Reaction mixture was refluxed at 70° C. for 2-3 h. The progress of the reaction was followed by TLC analysis on silica gel with 50% EtOAc-hexane as mobile phase. SM Rf=0.40 and Product Rf=0.5. Reaction mixture was poured into ice water (10 mL) slurry and compound was extracted with EtOAc (3×15 mL). The combined organic layers was washed with brine solution (3×15 mL), dried over MgSO4, filtered, and concentrated by rotary evaporation (25° C., 20 mmHg) to afford 0.28 g of Crude compound. evaporation (25° C., 20 mmHg) to afford 3.25 g of a yellow oil. The resulting crude compound was subjected to column purification. The crude reaction mixture was purified by column chromatography using silica 60/120 using ethyl acetate:hexane as mobile phase. The column (5×10 cm) was packed in hexane and started eluting in ethyl acetate in gradient manner starting with fraction collection (25-mL fractions) from 35% to 40% ethyl acetate in hexane. Compound started eluting with 35% ethylacetate in hexane. Fraction containing such TLC profile was collected together to obtain pure compound (50 mg), Yield (16.18%). 1H NMR (400 MHz, CDCl3) δ 10.3 (s, 1H), 8.50 (s, 1H), 8.46 (s, 1H), 7.74 (s, 1H), 7.63 (s, 1H) 7.50-7.53 (d, J=12 Hz, 1H) 7.01 (s, 1H) 6.27-6.30 (d, J=12 Hz, 1H) 4.65-4.71 (m, 1H) 1.39-1.40 (d, J=4 Hz, 6H) LCMS C11H7ClF3N3 (331.76)[M+1] found 331.85 at 3.910. (LCMS 99.67%).

Provenance & Evidence