1-amino-1,3-dimethylthiourea

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred, room temperature, solution of 2,4-dimethylthiosemicarbazide (5.96 g, 50.0 mmol) and dry pyridine (100 mL) was added dropwise 3-fluorobenzoyl chloride (7.93 g, 50.0 mmol). After stirring overnight, the reaction mixture was evaporated at reduced pressure. The concentrate was slurried with water and that which did not dissolve was collected by filtration. Crystallization of this material from ethanol afforded the desired product as colorless needles, mp 202°-205° C. the reaction mixture was evaporated at reduced pressure did not dissolve was collected by filtration Crystallization of this material from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 2,4-dimethylthiosemicarbazide (2.39 g, 2.00×10-2 mole) and pyridine (20 ml) was added dropwise 2-naphthoyl chloride. (3.89 g, 2.04×1031 2 mole) After stirring at room temperature for 48 hours the reaction was evaporated to dryness, affording a beige solid which was treated with H2O (100 ml). Filtration of the aqueous mixture gave the desired compound as a beige product, 5.47 g (100%). If pure 1-(2-naphthoyl)-2,4dimethylthiosemicarbazide is desired, the crude product is purified by crystallization. was evaporated to dryness affording a beige solid which Filtration of the aqueous mixture

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 2,4-dimethylthiosemicarbazide (2.39 g, 2.00×10-2 mole) and pyridine (20 ml) was added dropwise 2-naphthoyl chloride. (3.89 g, 2.04×1031 2 mole) After stirring at room temperature for 48 hours the reaction was evaporated to dryness, affording a beige solid which was treated with H2O (100 ml). Filtration of the aqueous mixture gave the desired compound as a beige product, 5.47 g (100%). If pure 1-(2-naphthoyl)-2,4dimethylthiosemicarbazide is desired, the crude product is purified by crystallization. was evaporated to dryness affording a beige solid which Filtration of the aqueous mixture

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2,4-dimethylthiosemicarbazide (0.20 g) and 2-(4-chloro-2-fluoro-5-methoxyphenyl)-2-oxoacetic acid (0.38 g) in methanol (10 ml) was refluxed for 16 hours. Filtration of the reaction mixture afforded 6-(4-chloro-2-fluoro-5-methoxy-phenyl)-2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine (0.28 g). 1H NMR, CDCl3, 3.77 (3H, s), 3.91 (3H, s), 4.07 (3H, s), 7.08 (1H, d, J=6.09 Hz), 7.25 (1H, d, J=9.22 Hz). Filtration of the reaction mixture

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2,4-dimethylthiosemicarbazide (0.20 g) and 2-(4-chloro-2-fluoro-5-methoxyphenyl)-2-oxoacetic acid (0.38 g) in methanol (10 ml) was refluxed for 16 hours. Filtration of the reaction mixture afforded 6-(4-chloro-2-fluoro-5-methoxy-phenyl)-2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine (0.28 g). 1H NMR, CDCl3, 3.77 (3H, s), 3.91 (3H, s), 4.07 (3H, s), 7.08 (1H, d, J=6.09 Hz), 7.25 (1H, d, J=9.22 Hz). Filtration of the reaction mixture

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred, room temperature, solution of 2,4-dimethylthiosemicarbazide (5.96 g, 50.0 mmol) and dry pyridine (100 mL) was added dropwise 3-fluorobenzoyl chloride (7.93 g, 50.0 mmol). After stirring overnight, the reaction mixture was evaporated at reduced pressure. The concentrate was slurried with water and that which did not dissolve was collected by filtration. Crystallization of this material from ethanol afforded the desired product as colorless needles, mp 202°-205° C. the reaction mixture was evaporated at reduced pressure did not dissolve was collected by filtration Crystallization of this material from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred, room temperature, solution of 2,4-dimethylthiosemicarbazide (5.96 g, 50.0 mmol) and dry pyridine (100 mL) was added dropwise 3-fluorobenzoyl chloride (7.93 g, 50.0 mmol). After stirring overnight, the reaction mixture was evaporated at reduced pressure. The concentrate was slurried with water and that which did not dissolve was collected by filtration. Crystallization of this material from ethanol afforded the desired product as colorless needles, mp 202°-205° C. the reaction mixture was evaporated at reduced pressure did not dissolve was collected by filtration Crystallization of this material from ethanol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4.0 g of 2,4-dimethyl-thiosemicarbazide and 6.7 g of 1-phenyl-4-chlorobutan-1-one in 165 ml of isopropanol is refluxed for 48 hours. The mixture is then allowed to cool to room temperature and stirred for an additional 48 hours. The solvent is evaporated, the residue is dissolved in methylene chloride, and the methylene chloride solution is washed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride and dried over sodium sulfate. Evaporation of the solvent leaves a brownish oil which crystallizes and is treated with hexane. The resulting greyish powder is purified by flash chromatography using 4% ethyl acetate/methylene chloride as eluent, followed by crystallization from hexane to give 5,6,7,7a-tetrahydro-1,3-dimethyl-7a-phenyl-1H-pyrrolo[1,2-b][1,2,4]triazole-2(3H)-thione as tiny colorless needles melting at about 83°-85° C. The solvent is evaporated the residue is dissolved in methylene chloride the methylene chloride solution is washed with saturated aqueous sodium bicarbonate and with saturated aqueous sodium chloride dried over sodium sulfate Evaporation of the solvent leaves a brownish oil which crystallizes is treated with hexane The resulting greyish powder is purified by flash chromatography followed by crystallization from hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred, room temperature, solution of 2,4-dimethylthiosemicarbazide (3.75 g, 3.15×10-2 mole) and pyridine (30 ml) was added dropwise 2-thiophenecarbonyl chloride (3.20 ml, 2.99×10-2 mole). After stirring overnight the pyridine was evaporated at reduced pressure and the concentrate was treated with H2O. The resulting semi-solid was extracted into ethyl acetate. The ethyl acetate extract was washed with saturated NaCl and subsequently dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure, leaving a slightly yellowish solid. This was treated with Et2O and the solid was collected by filtration affording a colorless powder: 4.7 g (68%), mp 176°-178° C. was evaporated at reduced pressure the concentrate was treated with H2O The resulting semi-solid was extracted into ethyl acetate The ethyl acetate extract was washed with saturated NaCl subsequently dried over anhydrous Na2SO4 The drying agent was removed by filtration the filtrate was evaporated at reduced pressure leaving a slightly yellowish solid the solid was collected by filtration affording a colorless powder

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 2,4-dimethylthiosemicarbazide (0.20 g) and 2-(4-chloro-2-fluoro-5-methoxyphenyl)-2-oxoacetic acid (0.38 g) in methanol (10 ml) was refluxed for 16 hours. Filtration of the reaction mixture afforded 6-(4-chloro-2-fluoro-5-methoxy-phenyl)-2,4-dimethyl-5-oxo-3-thioxo-2,3,4,5-tetrahydro-1,2,4-triazine (0.28 g). 1H NMR, CDCl3, 3.77 (3H, s), 3.91 (3H, s), 4.07 (3H, s), 7.08 (1H, d, J=6.09 Hz), 7.25 (1H, d, J=9.22 Hz). Filtration of the reaction mixture