3-Chloro-4-methylaniline → HCID 68422227, compound

Participants

Reaction Steps

4-Cyclopropyl-1,2,3-thiadiazolecarboxylic acid (4 g; 24 mmols), 2-chloro-1-methylpyridinium iodide (7.2 g; 28 mmols), triethylamine (5.9 g; 58 mmols) and 3-chloro-4-methylaniline (3.7 g; 26 mmols) were dissolved or suspended in THF (50 ml), followed by stirring at room temperature for 10 hours. Water was added thereto to stop the reaction, the mixture was extracted with ethyl acetate. After drying over anhydrous sodium sulfate, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to thereby obtain 6.9 g of 3′-chloro-4-cyclopropyl-4′-methyl-1,2,3-thiadiazole-5-carboxanilide.

Provenance & Evidence