3 -[(4-氯苯基)硫代]戊烷- 2,4 -二酮

反应条件: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A stirred suspension of the product of step 3 (0.333 g, 1.77 mmol) and 3-(4-chloro-phenylsulfanyl)-pentane-2,4-dione (0.473 g, 1.95 mmol) in n-propanol was heated at 95° C. overnight. The reaction solution was concentrated directly onto silica and flash chromatographed (methylene chloride/methanol) to afford a dirty yellow solid. This material was further purified by trituration with diethyl ether to afford 0.056 g (8%) of product as a white solid: 1H NMR (DMSO-d6) δ 9.44 (s, 1H), 8.94-8.77 (m, 1H), 8.68-8.43 (m, 1H), 8.18-7.96 (m, 1H), 7.77-7.57 (m, 1H), 7.45-7.24 (m, 2H), 7.20-6.98 (m, 2H), 2.83 (s, 3H), 2.20 (s, 3H) ppm. The reaction solution was concentrated directly onto silica and flash chromatographed (methylene chloride/methanol) to afford a dirty yellow solid This material was further purified by trituration with diethyl ether

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

实验步骤: A mixture of 3-amino-4-chlorophenol (5.0 g), 3-(4-chlorophenylsulfanyl)pentane-2,4-dione (8.4 g), p-toluenesulfonic acid monohydrate (3.20 g) and toluene (150 mL) was heated at reflux for 2 days. The mixture was cooled to room temperature and the solvent removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of dichloromethane and cyclohexane (1:9 by volume) gave title compound as a pale yellow solid, 0.99 g. was heated at reflux for 2 days the solvent removed under reduced pressure The residue was dissolved in ethyl acetate washed with water and saturated aqueous sodium chloride solution dried over magnesium sulfate The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel eluting with a mixture of dichloromethane and cyclohexane (1:9 by volume)

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-amino-4-chlorophenol (5.0 g), 3-(4-chlorophenylsulfanyl)pentane-2,4-dione (8.4 g), p-toluenesulfonic acid monohydrate (12 g) was heated at 140° C. for 6 hours. The mixture was cooled to room temperature and purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 1:1 by volume) to afford title compound as a brown solid, 1.3 g. The mixture was cooled to room temperature purified by column chromatography on silica gel eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 1:1 by volume)

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-amino-4-chlorophenol (0.36 g), 3-(4-chlorophenylsulfanyl)pentane-2,4-dione (0.61 g) and p-toluenesulfonic acid monohydrate (0.040 g) was heated at 140° C. for 10 hours. The mixture was cooled to room temperature and purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 0:1 by volume) to afford title compound as a brown oil, 0.050 g. The mixture was cooled to room temperature purified by column chromatography on silica gel eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 0:1 by volume)

反应条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-amino-4-chlorophenol (0.36 g), 3-(4-chlorophenylsulfanyl)pentane-2,4-dione (0.61 g) and p-toluenesulfonic acid monohydrate (0.040 g) was heated at 140° C. for 10 hours. The mixture was cooled to room temperature and purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 0:1 by volume) to afford title compound as a brown oil, 0.050 g. The mixture was cooled to room temperature purified by column chromatography on silica gel eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 0:1 by volume)

反应条件: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A stirred suspension of the product of step 3 (0.333 g, 1.77 mmol) and 3-(4-chloro-phenylsulfanyl)-pentane-2,4-dione (0.473 g, 1.95 mmol) in n-propanol was heated at 95° C. overnight. The reaction solution was concentrated directly onto silica and flash chromatographed (methylene chloride/methanol) to afford a dirty yellow solid. This material was further purified by trituration with diethyl ether to afford 0.056 g (8%) of product as a white solid: 1H NMR (DMSO-d6) δ 9.44 (s, 1H), 8.94-8.77 (m, 1H), 8.68-8.43 (m, 1H), 8.18-7.96 (m, 1H), 7.77-7.57 (m, 1H), 7.45-7.24 (m, 2H), 7.20-6.98 (m, 2H), 2.83 (s, 3H), 2.20 (s, 3H) ppm. The reaction solution was concentrated directly onto silica and flash chromatographed (methylene chloride/methanol) to afford a dirty yellow solid This material was further purified by trituration with diethyl ether

反应条件: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A stirred suspension of the product of step 3 (0.333 g, 1.77 mmol) and 3-(4-chloro-phenylsulfanyl)-pentane-2,4-dione (0.473 g, 1.95 mmol) in n-propanol was heated at 95° C. overnight. The reaction solution was concentrated directly onto silica and flash chromatographed (methylene chloride/methanol) to afford a dirty yellow solid. This material was further purified by trituration with diethyl ether to afford 0.056 g (8%) of product as a white solid: 1H NMR (DMSO-d6) δ 9.44 (s, 1H), 8.94–8.77 (m, 1H), 8.68–8.43 (m, 1H), 8.18–7.96 (m, 1H), 7.77–7.57 (m, 1H), 7.45–7.24 (m, 2H), 7.20–6.98 (m, 2H), 2.83 (s, 3H), 2.20 (s, 3H) ppm. The reaction solution was concentrated directly onto silica and flash chromatographed (methylene chloride/methanol) to afford a dirty yellow solid This material was further purified by trituration with diethyl ether

反应条件: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A stirred suspension of the product of step 3 (0.333 g, 1.77 mmol) and 3-(4-chloro-phenylsulfanyl)-pentane-2,4-dione (0.473 g, 1.95 mmol) in n-propanol was heated at 95° C. overnight. The reaction solution was concentrated directly onto silica and flash chromatographed (methylene chloride/methanol) to afford a dirty yellow solid. This material was further purified by trituration with diethyl ether to afford 0.056 g (8%) of product as a white solid: 1H NMR (DMSO-d6) δ 9.44 (s, 1H), 8.94-8.77 (m, 1H), 8.68-8.43 (m, 1H), 8.18-7.96 (m, 1H), 7.77-7.57 (m, 1H), 7.45-7.24 (m, 2H), 7.20-6.98 (m, 2H), 2.83 (s, 3H), 2.20 (s, 3H) ppm. The reaction solution was concentrated directly onto silica and flash chromatographed (methylene chloride/methanol) to afford a dirty yellow solid This material was further purified by trituration with diethyl ether

反应条件: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A stirred suspension of the product of step 3 (0.333 g, 1.77 mmol) and 3-(4-chloro-phenylsulfanyl)-pentane-2,4-dione (0.473 g, 1.95 mmol) in n-propanol was heated at 95° C. overnight. The reaction solution was concentrated directly onto silica and flash chromatographed (methylene chloride/methanol) to afford a dirty yellow solid. This material was further purified by trituration with diethyl ether to afford 0.056 g (8%) of product as a white solid: 1H NMR (DMSO-d6) δ 9.44 (s, 1H), 8.94-8.77 (m, 1H), 8.68-8.43 (m, 1H), 8.18-7.96 (m, 1H), 7.77-7.57 (m, 1H), 7.45-7.24 (m, 2H), 7.20-6.98 (m, 2H), 2.83 (s, 3H), 2.20 (s, 3H) ppm. The reaction solution was concentrated directly onto silica and flash chromatographed (methylene chloride/methanol) to afford a dirty yellow solid This material was further purified by trituration with diethyl ether