Propanal → HCID 58896420, compound

Participants

Reaction Conditions

Reaction Steps

To 0.29 g (0.87 mmol) of 1-[3-amino-5-fluoro-2-(methylamino)phenyl]-3-mesitylthiourea in 15 mL of acetonitrile was added 1.09 mL (7.9 mmol) of triethylamine followed by 0.4 g (1.5 mmol) of mercuric chloride. After 2h at room temperature an additional 0.7 g (2.6 mmol) of mercuric chloride was added. After 2 h of additional reaction time, the mixture was diluted with water and the resulting crude 5-fluoro-N2-mesityl-1-methyl-1H-benzoimidazole-2,7-diamine was collected as a brown precipitate via filtration. The crude product thus obtained was slurried in 50 mL of methanol and treated with 1.6 mL (22 mmol) of propionaldehyde, 3 mL of glacial acetic acid and 1.1 g (17 mmol) of sodium cyanoborohydride. The mixture was stirred at 50° C. for 24 h. The reaction mixture was cooled to room temperature and the volatiles were removed in vacuo. The crude solid was mixed with water and made basic with saturated potassium carbonate. The mixture was partioned with ethyl acetate and separated. The organic layer was washed with brine, dried over sodium sulfate, filtered, concentrated onto silica gel and purified by flash chromatography eluting with a 75% hexanes/ethyl acetate mixture to give impure title compound. The impure material was slurried in hexanes and 0.065 g (20%) of the title compound was collected as a white solid.

Provenance & Evidence