* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With ammonium chloride;trimethylaluminum; In hexane; chloroform; toluene;
EXAMPLE 4A 2-Ethoxybenzamidine hydrochloride 21.4 g (400 mmol) of ammonium chloride are suspended in 375 ml of toluene, and the suspension is cooled to 0 C. 200 ml of a 2M solution of trimethylaluminium in hexane are added dropwise, and the mixture is stirred at room temperature until the evolution of gas has ceased. After addition of 29.44 g (200 mmol) of <strong>[6609-57-0]2-ethoxybenzonitrile</strong>, the reaction mixture is stirred at 80 C. (bath) overnight. With ice-cooling, the cooled reaction mixture is added to a suspension of 100 g of silica gel and 950 ml of chloroform, and the mixture is stirred at room temperature for 30 minutes. The mixture is filtered off with suction, and the filter residue is washed with the same amount of methanol. The mother liquor is concentrated, the resulting residue is stirred with a mixture of dichloromethane and methanol (9:1), the solid is filtered off with suction and the mother liquor is concentrated. This gives 30.4 g (76%) of a colourless solid. 200 MHz 1H-NMR (DMSO-d6): 1.36, t, 3H; 4.12, quart., 2H; 7.10, t, 1H; 7.21, d, 1H; 7.52, m, 2H; 9.30, s, broad, 4H.
With ammonium chloride;trimethylaluminum; In hexane; chloroform; toluene;
EXAMPLE 12A 2-Ethoxy-benzamidine hydrochloride 21.4 g (400 mmol) of ammonium chloride are suspended in 375 ml of toluene, and the suspension is cooled to 0 C. 200 ml of a 2M solution of trimethylaluminium in hexane are added dropwise, and the mixture is stirred at room temperature until evolution of gas has ceased. 29.44 g (200 mmol) of <strong>[6609-57-0]2-ethoxybenzonitrile</strong> are added, and the reaction mixture is then stirred at 80 C. (bath) overnight. The cooled reaction mixture is, with ice-cooling, added to a suspension of 100 g of silica gel and 950 ml of chloroform, and the mixture is stirred at room temperature for 30 minutes. The mixture is filtered off with suction and the filter residue is washed with the same amount of methanol. The mother liquor is evaporated, the resulting residue is stirred with a mixture of dichloromethane and methanol (9:1), the solid is filtered off with suction and the mother liquor is evaporated. This gives 30.4 g (76%) of a colourless solid. 200 MHz 1H-NMR (DMSO-d6): 1.36 (t, 3H); 4.12 (quart., 2H); 7.10 (t, 1H); 7.21 (d, 1H); 7.52 (m, 2H); 9.30 (s, broad, 4H).
NH4Cl (1.26 g, 23.52 mmoles) is introduced in a 100 ml round bottom flask and suspended in 16 ml of anhydrous toluene under argon atmosphere . The mixture is cooled in an ice bath and 2N Al (CH3) 3 (12 ml) in toluene are added dropwise, keeping under stirring for 30' at room temperature. 2-Ethoxybenzonitrile (Ig) is added and the reaction is refluxed with stirring for 9 hours. Silica (0.8g) and then methanol (8 ml) are added to the mixture of reaction to eliminate the excess of Al (CH3) 3. The suspension is diluted with 8 ml of dichloromethane and then filtered washing the obtained solid several times <n="23"/>with methanol .The filtered solution is acidified with cone. HCl and evaporated to dryness. The obtained residue is treated with 12 ml of a mixture of dichlorometane/methanol (9:1), filtered and the organic solution evaporated to dryness . The residue is washed with ether.
With ammonium chloride; In hexane; chloroform; toluene;
EXAMPLE III 2-Ethoxy-benzamidine hydrochloride 21.4 g (400 mmol) of ammonium chloride are suspended in 375 ml of toluene and the suspension is cooled down to 0 C. 200 ml of a 2 M solution of trimethylaluminum in hexane are added dropwise and the mixture is stirred at room temperature until the evolution of gas has come to an end. After 29.44 g (200 mmol) of <strong>[6609-57-0]2-ethoxybenzonitrile</strong> (example II) have been added, the reaction mixture is stirred overnight at 80 C. (bath). Having been cooled down, the reaction mixture is added, while cooling with ice, to a suspension consisting of 100 g of silica gel and 950 ml of chloroform and the mixture is stirred at room temperature for 30 minutes. Filtration with suction is carried out and the subsequent washing takes place with the same quantity of methanol. The mother liquor is evaporated and the resulting residue is stirred up with a mixture of dichloromethane and methanol (9:1), after which the solid is filtered off with suction and the mother liquor is evaporated. 3.4 g (76%) of a colorless solid are obtained. 200 MHz 1H-NMR (DMSO-D6): 1.36, t, 3H; 4.12, quart., 2H; 7.10, t, 1H; 7.21, d, 1H; 7.52, m, 2H; 9.30, s, broad, 4H.
With ammonium chloride; In hexane; chloroform; toluene;
EXAMPLE 13A 2-Ethoxybenzamidine hydrochloride 21.4 g (400 mmol) of ammonium chloride are suspended in 375 ml of toluene, and the suspension is cooled to 0 C. 200 ml of a 2 M solution of trimethylaluminum in hexane are added dropwise, and the mixture is stirred at room temperature until the evolution of gas has ceased. Following addition of 29.44 g (200 mmol) of <strong>[6609-57-0]2-ethoxybenzonitrile</strong>, the reaction mixture is stirred at 80 C. (bath) overnight. The cooled reaction mixture is, with ice-cooling, added to a suspension of 100 g of silica gel and 950 ml of chloroform, and the mixture is stirred at room temperature for 30 minutes. The mixture is filtered off with suction and the filter cake is washed with the same amount of methanol. The mother liquor is concentrated, the resulting residue is triturated with a mixture of dichloromethane and methanol (9:1), the solid is filtered off with suction and the mother liquor is concentrated. This gives 30.4 g (76%) of a colorless solid. 200 MHz 1H-NMR (DMSO-d6): 1.36 (t, 3H); 4.12 (quart., 2H); 7.10 (t, 1H); 7.21 (d, 1H); 7.52 (m, 2H); 9.30 (s, broad, 4H).
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