-
11
-
-
84855929757
-
-
4 was filtered out, the filtrate was removed in vacuo. The residue was purified by column chromatography (silica gel, gradient elution with hexane: EtOAc (v/v) = 1:10-1:5) to give the corresponding product
-
4 was filtered out, the filtrate was removed in vacuo. The residue was purified by column chromatography (silica gel, gradient elution with hexane: EtOAc (v/v) = 1:10-1:5) to give the corresponding product.
-
-
-
-
12
-
-
84855924326
-
-
Methyl 5-amino-2-substituted benzoate 3. General procedure: To a solution of compound 2 (8 mmol) in ethanol (60 mL) was added stannous chloride dehydrate (0.99 g, 48 mmol). The mixture was stirred at 70 °C for 7 h, and half of the solvent was removed in vacuo. The residue was added ethyl acetate (3 mL × 40 mL). The organic layer was washed with aqueous solution of sodium hydroxide, dried with anhydrous sodium sulfate, and evaporated in vacuo. Chromatography the residue on silica gel gave the title compounds
-
Methyl 5-amino-2-substituted benzoate 3. General procedure: To a solution of compound 2 (8 mmol) in ethanol (60 mL) was added stannous chloride dehydrate (0.99 g, 48 mmol). The mixture was stirred at 70 °C for 7 h, and half of the solvent was removed in vacuo. The residue was added ethyl acetate (3 mL × 40 mL). The organic layer was washed with aqueous solution of sodium hydroxide, dried with anhydrous sodium sulfate, and evaporated in vacuo. Chromatography the residue on silica gel gave the title compounds.
-
-
-
-
13
-
-
84855911822
-
-
(Z)-4-((5-substitued-2- thioxoimidazolidin-4- ylidene)methyl)benzoic acid 6. General procedure: 4-Formylbenzoic acid 4 (10.0 g, 67 mmol) with anhydrous sodium acetate (22.0 g, 268 mmol) were successively added to a stirred solution of 2-substitued-imidazolidin-4-one 5 (70 mmol) in acetic acid (300 mL). The mixture was stirred at 120 °C for 0.5 h and then poured into water. The resulting mixture was stood overnight to form the precipitation. The crude solid was collected through filtration and air dried. The crude solid was crystallized twice with EtOAc to give pure compound
-
(Z)-4-((5-substitued-2-thioxoimidazolidin-4-ylidene)methyl)benzoic acid 6. General procedure: 4-Formylbenzoic acid 4 (10.0 g, 67 mmol) with anhydrous sodium acetate (22.0 g, 268 mmol) were successively added to a stirred solution of 2-substitued-imidazolidin-4-one 5 (70 mmol) in acetic acid (300 mL). The mixture was stirred at 120 °C for 0.5 h and then poured into water. The resulting mixture was stood overnight to form the precipitation. The crude solid was collected through filtration and air dried. The crude solid was crystallized twice with EtOAc to give pure compound.
-
-
-
-
14
-
-
84855911821
-
-
(Z)-Methyl-2-substituted-5-(4-((2-substitued-5 -oxoimidazolidin- 4-ylidene)methyl)benzamido)benzoate 7. General procedure: To a stirred solution of compoud 6 (4 mmol) and compound 3 (4 mmol) in anhydrous DMF (50 mL), were successively added EDC hydrochloride with DIEA and HOBT. The mixture was stirred at 40 °C for 24-48 h and then poured into water. The resulting mixture was stood overnight to form the precipitation. The solid was collected through filtration and air crystallized twice with MeOH to give the title compound.
-
(Z)-Methyl-2-substituted-5-(4-((2-substitued-5-oxoimidazolidin-4-ylidene) methyl)benzamido)benzoate 7. General procedure: To a stirred solution of compoud 6 (4 mmol) and compound 3 (4 mmol) in anhydrous DMF (50 mL), were successively added EDC hydrochloride with DIEA and HOBT. The mixture was stirred at 40 °C for 24-48 h and then poured into water. The resulting mixture was stood overnight to form the precipitation. The solid was collected through filtration and air crystallized twice with MeOH to give the title compound.
-
-
-
-
15
-
-
84855968936
-
-
4), filtered, and crystallized twice with EtOAc to give pure 8a-g
-
4), filtered, and crystallized twice with EtOAc to give pure 8a-g.
-
-
-
|
