Hydrochloric Acid → HCID 178439384, compound

Participants

Reaction Steps

was prepared according to general procedure (A); 77 μg 3,5-diisopropyl-N,N-dimethylbenzene-1,4-diamine (0.35 mmol, 1 equiv), 39 μl formalin (0.53 mmol, 1.5 equiv), 0.23 mL 3.05 M hydrochloric acid in ethanol (0.70 mmol, 2 equiv) and 34 μl picolinaldehyde (0.35 mmol, 1 equiv) were combined in 1.8 mL ethanol and maintained at room temperature for 12 hours. The reaction was concentrated in vacuo and dried under high vacuum at 0.2 Torr. The crude material was then dissolved in 2.5 mL ethanol and stirred with 0.8 g sodium bicarbonate for 30 minutes at room temperature. The resulting suspension was then filtered through a 0.2 um nylon syringe tip filter. The solid sodium bicarbonate was washed with ethanol three times using 0.5 mL of ethanol for each wash and filtered. The combined filtrate was concentrated. The resulting crude oil was dissolved in 3.0 mL methanol and 0.12 g sodium tetraphenylborate (0.35 mmol, 1 equiv) in 1.0 mL methanol was added drop wise while stirring vigorously. The mixture was cooled to 4° C. in a refrigerator. The methanol was then decanted, and the solid was rinsed with methanol three times using 0.25 mL of methanol for each rinse and dried under high vacuum at 0.2 Torr to obtain 0.16 g 2-(4-(dimethylamino)-2,6-diisopropylphenyl)-2H-imidazo[1,5-a]pyridin-4-ium tetraphenylborate (0.26 mmol, a 73% yield) as a dark brown solid.

Provenance & Evidence