3-苯基-2-硫酮-1,3-噻唑啉-4-酮

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 8.4 g. (0.04 m.) of 3-phenylrhodanine, 21 g. (0.12 m.) of triethylorthopropionate and 80 ml. of acetic anhydride is heated under reflux for six hours, cooled and filtered. The solid is washed with 50% aqueous acetic acid to afford 5-(1'-ethoxypropylidene)-3-phenylrhodanine, m.p. 178°-181°C. A mixture of 8.4 g under reflux for six hours cooled filtered The solid is washed with 50% aqueous acetic acid

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Alternatively, a mixture of 6 g. (0.029 m.) of 3-phenyl-rhodanine, 15 g. (0.063 m.) of triethylorthophenylacetate and 15 ml. of n-butyl ether is heated to reflux and then distillate is removed until the temperature of the mixture reaches 150°C. After heating at this temperature for one hour, an additional 5 g. of orthoester is added and heating is continued for 30 minutes. To the reaction mixture is added 5 ml. of acetic anhydride and heating is continued for 5 minutes. The resulting mixture is concentrated in vacuo and the residue is eluted through a column of silica gel with 2:1-cyclohexane-benzene. The product from the first eluates give 5-(1'-ethoxy-2'-phenylethylidene)-3-phenylrhodanine, m.p. 119°-121°C. Alkaline hydrolysis as described above of this intermediate furnishes the identical hydroxy derivative. Alternatively, a mixture of 6 g to reflux distillate is removed until the temperature of the mixture reaches 150°C After heating at this temperature for one hour of orthoester is added heating To the reaction mixture is added 5 ml of acetic anhydride and heating is continued for 5 minutes The resulting mixture is concentrated in vacuo the residue is eluted through a column of silica gel with 2

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 25 g. (0.12 m.) of 3-phenylrhodanine, 80 g. (0.34 m.) of triethylorthophenylacetate [prepared as described in J.A.C.S. 68, 1917 (1946)] and 250 ml. of acetic anhydride is heated under reflux for 20 hours and the solution is then concentrated in vacuo. The residue is filtered and the solid is stirred with 160 ml. of dioxane, 160 ml. of water and 40 ml. of 10% sodium hydroxide for 4 hours. The solution is concentrated in vacuo at 35°-40°C. to evaporate the dioxane. The aqueous solution, after washing with ether and decolorizing with charcoal, is made acidic with dilute hydrochloric acid. The solid product is purified by chromatography to give 5-(1'-hydroxy-2'-phenylethylidene)-3-phenyl-rhodanine, m.p. 146-148°C. A mixture of 25 g (0.34 m.) of triethylorthophenylacetate [prepared as described in J.A.C.S. 68, 1917 (1946)] and 250 ml under reflux for 20 hours the solution is then concentrated in vacuo The residue is filtered The solution is concentrated in vacuo at 35°-40°C. to evaporate the dioxane The aqueous solution, after washing with ether The solid product is purified by chromatography