3-METHOXYBENZAMIDINE HYDROCHLORIDE

White solid

General procedure: A mixture of ynal 1 (0.5 mmol), amidine hydrochloride 2 (0.6 mmol), K2CO3(1.0 mmol), and MCM-41-PPh3-AuCl (41 mg, 0.015 mmol) in DCM (3mL) was stirred at room temperature for 3 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (15 mL) and filtered. The gold catalyst was washed with distilled water(5 mL), and dry ethanol (25mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silicagel (eluent: petroleum ether/ethyl acetate) to afford the desired product 3.General procedure: A mixture of ynal 1 (0.5 mmol), amidine hydrochloride 2 (0.6 mmol), K2CO3(1.0 mmol), and MCM-41-PPh3-AuCl (41 mg, 0.015 mmol) in DCM (3mL) was stirred at room temperature for 3 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (15 mL) and filtered. The gold catalyst was washed with distilled water(5 mL), and dry ethanol (25mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silicagel (eluent: petroleum ether/ethyl acetate) to afford the desired product 3.The reaction bottle by adding 1 b (4 mmol), two chlorofluorcarbons sodium acetate (4 mmol), cesium carbonate (8 mmol) and acetonitrile (10 ml), then in 120 C heating reaction 24 hours. After the reaction is finished using water quenching, and then the extraction of ethyl acetate, the combined organic phase after drying with anhydrous sodium sulfate, concentrated using petroleum ether and ethyl acetate mixed solvent of column chromatography to obtain the product 3 b, yield is 76%. White solidGeneral procedure: The corresponding amidine or amidine salt 12'14, 18, 19 (0.51 mmol) and Et3N (0.8 ml, 1.1 mmol) were added to a solution of alkynones 5, 6 (0.36 mmol) in i-PrOH (6 ml). The reaction mixture was heated under reflux for 8 h and cooled to room temperature. The reaction mixture was then concentrated under reduced pressure, and CHCl3 (15 ml) was added to the residue. The obtained solution was washed with water (3×10 ml) and dried over Na2SO4. The drying agent was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluent CHCl3'EtOH, gradient from 100:0 to 100:5. Fractions with Rf 0.4 (CHCl3'EtOH, 20:1) were pooled, and the solvent was removed under reduced pressure

Molecular Weight:186.64
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:186.0559907
Monoisotopic Mass:186.0559907
Topological Polar Surface Area:59.1
Heavy Atom Count:12
Complexity:147
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes