4-oxopentanoyl chloride

反応条件: temp:0.00; pressure:0.00; stir:

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 well stirred suspension of anhydrous aluminium chloride (27.0 g, 205.9 mmol) in 126 ml of benzene was added 4-oxopentanoylchloride (23.0 g, 171.6 mmol) drop-wise, over a period of 30-35 minutes at room temperature (25-30° C.). The reaction mixture was stirred at the same temperature for 1 hour. After decomposition of the reaction mixture by the addition of solid ice and hydrochloric acid (10 ml) the precipitated solid was filtered and the filtrate evaporated on a rotary evaporator to remove all the solvents. The residue was dissolved in ethyl acetate (400 ml), washed with water (2×100 ml), brine (100 ml) and dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product so obtained was chromatographed over silica gel (100-200 mesh) using chloroform as eluent to give 8.6 g (24.07%) of the title compound. The reaction mixture was stirred at the same temperature for 1 hour was filtered the filtrate evaporated on a rotary evaporator to remove all the solvents The residue was dissolved in ethyl acetate (400 ml) washed with water (2×100 ml), brine (100 ml) dried over anhydrous sodium sulfate the solvent evaporated off The crude product so obtained was chromatographed over silica gel (100-200 mesh)

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

実験手順: To a well stirred suspension of anhydrous aluminium chloride (29.66 g, 0.223 mol) in 154.7 ml of chlorobenzene was added 4-oxopentanoylchloride (25.0 g, 0.187 mol) drop-wise, over a period of 30-35 minutes at room temperature (25-30° C.). The reaction mixture was stirred at the same temperature for 1 hour. After decomposition of the reaction mixture by the addition of solid ice and hydrochloric acid (10 ml) the precipitated solid was filtered and filtrate was concentrated in a rotary evaporation to remove all the solvents. The residue was dissolved in ethyl acetate (400 ml), washed with water (2×100 ml), brine (100 ml). The organic layer was dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product so obtained was chromatographed over silica gel (100-200 mesh) using chloroform-hexane (90:10) as eluent to give 5.3 g (13.60%) of the title compound. The reaction mixture was stirred at the same temperature for 1 hour was filtered filtrate was concentrated in a rotary evaporation to remove all the solvents The residue was dissolved in ethyl acetate (400 ml) washed with water (2×100 ml), brine (100 ml) The organic layer was dried over anhydrous sodium sulfate the solvent evaporated off The crude product so obtained was chromatographed over silica gel (100-200 mesh)

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

実験手順: To a well stirred suspension of anhydrous aluminium chloride (29.66 g, 0.223 mol) in 154.7 ml of chlorobenzene was added 4-oxopentanoylchloride (25.0 g, 0.187 mol) drop-wise, over a period of 30-35 minutes at room temperature (25-30° C.). The reaction mixture was stirred at the same temperature for 1 hour. After decomposition of the reaction mixture by the addition of solid ice and hydrochloric acid (10 ml) the precipitated solid was filtered and filtrate was concentrated in a rotary evaporation to remove all the solvents. The residue was dissolved in ethyl acetate (400 ml), washed with water (2×100 ml), brine (100 ml). The organic layer was dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product so obtained was chromatographed over silica gel (100-200 mesh) using chloroform-hexane (90:10) as eluent to give 5.3 g (13.60%) of the title compound. The reaction mixture was stirred at the same temperature for 1 hour was filtered filtrate was concentrated in a rotary evaporation to remove all the solvents The residue was dissolved in ethyl acetate (400 ml) washed with water (2×100 ml), brine (100 ml) The organic layer was dried over anhydrous sodium sulfate the solvent evaporated off The crude product so obtained was chromatographed over silica gel (100-200 mesh)

反応条件: temp:0.00; pressure:0.00; stir:

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 well stirred suspension of anhydrous aluminium chloride (27.0 g, 205.9 mmol) in 126 ml of benzene was added 4-oxopentanoylchloride (23.0 g, 171.6 mmol) drop-wise, over a period of 30-35 minutes at room temperature (25-30° C.). The reaction mixture was stirred at the same temperature for 1 hour. After decomposition of the reaction mixture by the addition of solid ice and hydrochloric acid (10 ml) the precipitated solid was filtered and the filtrate evaporated on a rotary evaporator to remove all the solvents. The residue was dissolved in ethyl acetate (400 ml), washed with water (2×100 ml), brine (100 ml) and dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product so obtained was chromatographed over silica gel (100-200 mesh) using chloroform as eluent to give 8.6 g (24.07%) of the title compound. The reaction mixture was stirred at the same temperature for 1 hour was filtered the filtrate evaporated on a rotary evaporator to remove all the solvents The residue was dissolved in ethyl acetate (400 ml) washed with water (2×100 ml), brine (100 ml) dried over anhydrous sodium sulfate the solvent evaporated off The crude product so obtained was chromatographed over silica gel (100-200 mesh)

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

実験手順: To a well stirred suspension of anhydrous aluminium chloride (27.0 g, 205.9 mmol) in 126 ml of benzene was added 4-oxopentanoylchloride (23.0 g, 171.6 mmol) drop-wise, over a period of 30-35 minutes at room temperature (25-30° C.). The reaction mixture was stirred at the same temperature for 1 hour. After decomposition of the reaction mixture by the addition of solid ice and hydrochloric acid (10 ml) the precipitated solid was filtered and the filtrate evaporated on a rotary evaporator to remove all the solvents. The residue was dissolved in ethyl acetate (400 ml), washed with water (2×100 ml), brine (100 ml) and dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product so obtained was chromatographed over silica gel (100-200 mesh) using chloroform as eluent to give 8.6 g (24.07%) of the title compound. The reaction mixture was stirred at the same temperature for 1 hour was filtered the filtrate evaporated on a rotary evaporator to remove all the solvents The residue was dissolved in ethyl acetate (400 ml) washed with water (2×100 ml), brine (100 ml) dried over anhydrous sodium sulfate the solvent evaporated off The crude product so obtained was chromatographed over silica gel (100-200 mesh)

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

実験手順: To a well stirred suspension of anhydrous aluminium chloride (27.0 g, 205.9 mmol) in 126 ml of benzene was added 4-oxopentanoylchloride (23.0 g, 171.6 mmol) drop-wise, over a period of 30-35 minutes at room temperature (25-30° C.). The reaction mixture was stirred at the same temperature for 1 hour. After decomposition of the reaction mixture by the addition of solid ice and hydrochloric acid (10 ml) the precipitated solid was filtered and the filtrate evaporated on a rotary evaporator to remove all the solvents. The residue was dissolved in ethyl acetate (400 ml), washed with water (2×100 ml), brine (100 ml) and dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product so obtained was chromatographed over silica gel (100-200 mesh) using chloroform as eluent to give 8.6 g (24.07%) of the title compound. The reaction mixture was stirred at the same temperature for 1 hour was filtered the filtrate evaporated on a rotary evaporator to remove all the solvents The residue was dissolved in ethyl acetate (400 ml) washed with water (2×100 ml), brine (100 ml) dried over anhydrous sodium sulfate the solvent evaporated off The crude product so obtained was chromatographed over silica gel (100-200 mesh)

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

実験手順: To a well stirred suspension of anhydrous aluminium chloride (29.66 g, 0.223 mol) in 154.7 ml of chlorobenzene was added 4-oxopentanoylchloride (25.0 g, 0.187 mol) drop-wise, over a period of 30-35 minutes at room temperature (25-30° C.). The reaction mixture was stirred at the same temperature for 1 hour. After decomposition of the reaction mixture by the addition of solid ice and hydrochloric acid (10 ml) the precipitated solid was filtered and filtrate was concentrated in a rotary evaporation to remove all the solvents. The residue was dissolved in ethyl acetate (400 ml), washed with water (2×100 ml), brine (100 ml). The organic layer was dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product so obtained was chromatographed over silica gel (100-200 mesh) using chloroform-hexane (90:10) as eluent to give 5.3 g (13.60%) of the title compound. The reaction mixture was stirred at the same temperature for 1 hour was filtered filtrate was concentrated in a rotary evaporation to remove all the solvents The residue was dissolved in ethyl acetate (400 ml) washed with water (2×100 ml), brine (100 ml) The organic layer was dried over anhydrous sodium sulfate the solvent evaporated off The crude product so obtained was chromatographed over silica gel (100-200 mesh)

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

実験手順: 4-oxopentanoyl chloride (0.378 g, 2.8 mmol) was added to a suspension of N-methyl-5-(3-pyridyl)-1,3,4-thiadiazol-2-amine (0.3 g, 1.6 mmol) and 4-N,N-dimethylaminopyridine (0.229 g, 1.9 mmol) in dichloroethane (5 mL), stirred under nitrogen at room temperature for 30 minutes, refluxed for 14 hours, cooled, diluted with dichloroethane (50 mL) and washed with saturated aqueous sodium bicarbonate (70 mL). The aqueous layer was extracted with dichloroethane (30 mL) and the combined organic layers were dried over MgSO4, adsorbed on silica, applied to a Michel-Miller column and eluted with 9:1 ethyl acetate/hexane. The major fraction was collected and recrystallized from ethyl acetate/hexane to afford yellow needles. Yield 0.21 g (46%): mp 146-147° C.; IR (KBr, thin film) 1701, 1659 cm−1; 1HNMR (400 MHz, CDCl3) δ 9.13 (d, J=1.8 Hz, 1H), 8.69 (dd, J=4.8, 1.5 Hz, 1H), 8.28 (dt, J=6.2, 1.9 Hz, 1H), 7.42 (dd, J=8.0, 5.1 Hz, 1H), 3.90 (s, 3H), 2.96 (br, 4H), 2.29 (s, 3H); ESIMS m/z 291 ([M+H]+). refluxed for 14 hours cooled washed with saturated aqueous sodium bicarbonate (70 mL) The aqueous layer was extracted with dichloroethane (30 mL) the combined organic layers were dried over MgSO4 eluted with 9:1 ethyl acetate/hexane The major fraction was collected recrystallized from ethyl acetate/hexane to afford yellow needles