4-Aminobenzonitrile → HCID 18412521, compound

Participants

Reaction Steps

To a solution of 0.73 g (1.88 mmol) of 1-methyl-2-methoxymethylthieno[2,3-d]imidazol-5-yl-carboxylic acid-N-phenyl-N-(2-methoxycarbonylethyl)amide in 30 mL of methylene chloride were added dropwise at 5° C. 2.9 mL (2.9 mmol) of a 1-molar solution of boron tribromide in methylene chloride. After 16 hours stirring at ambient temperature, the mixture was washed with 20 mL of saturated sodium hydrogen carbonate solution, the organic phase was separated off, dried with sodium sulfate and filtered. The filtrate was mixed with 14 mL of N-ethyldiisopropylamine and 0.43 g (3.64 mmol) of 4-aminobenzonitrile. Then the methylene chloride was distilled off in vacuo, the residue obtained was heated to 50° C. for 1 hour and then the residual solvent was distilled off in vacuo. After chromatography (silica gel; methylene chloride/ethanol=99:1 to 97:3), a yellow oil was obtained which slowly solidified. Yield: 0.37 g (42% of theory); Rf value: 0.29 (silica gel; methylene chloride/ethanol=50:1+a few drops of ammonia).

Provenance & Evidence