正丁基硫脲

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

实验步骤: N-Butylthiourea is treated with oxalyl chloride to give 1-butyl-2-thioxo-4,5-imidazolidinedione which when substituted for 1-methyl-2-thioxo-4,5-imidazolidinedione in the procedure of Example 1 gives S-[5-(N'-butylthioureido)pentyl]isothiourea.

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

实验步骤: N-Butylthiourea is treated with oxalyl chloride to give 1-butyl-2-thioxo-4,5-imidazolidinedione which when substituted for 1-methyl-2-thioxo-4,5-imidazolidinedione in the procedure of Example 1 gives S-[5-(N'-butylthioureido)pentyl]isothiourea.

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of sodium 5-oxo-5,6-dihydro-2H-pyran-3-olate (Li, Wenke; Wayne, Gregory S.; Lallaman, John E.; Wittenberger, Steven J. J. Org. Chem. (2006), 71, 1725-1727) (1.36 g, 10 mmol) and n-butylthiourea (Trans World) (1.32 g, 10 mmol) in tetrahydrofuran (15 mL) was added a mixture of DMSO/12 N HCl (1/1 molar ratio, 4.6 mL, 30 mmol). The reaction mixture was heated at 40° C. for overnight, and then cooled. The mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic extract was dried (MgSO4), filtered and concentrated. The residue was dried under vacuum for 12 h and dissolved in tetrahydrofuran (40 mL). To the solution was added 5-chloro-2-methoxy-benzoic acid (1.86 g, 10.0 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodimide hydrochloride (1.91 g, 10.0 mmol), 1-hydroxybenzotriazole (1.35 g, 10.0 mmol) and triethylamine (3.5 mL, 3.5 mmol). The mixture was stirred overnight at 80° C. and then cooled at room temperature. The mixture was diluted with ethyl acetate, washed with 1 M aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (SiO2, 0-75% ethyl acetate in hexanes) to afford 412 mg of the title compound. MS (ESI+) m/z 395 (M+H)+ was added cooled washed with aqueous sodium bicarbonate The organic extract was dried (MgSO4) filtered concentrated The residue was dried under vacuum for 12 h dissolved in tetrahydrofuran (40 mL) cooled at room temperature washed with 1 M aqueous NaHCO3 dried (Na2SO4) filtered concentrated The residue was purified by flash chromatography (SiO2, 0-75% ethyl acetate in hexanes)

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of sodium 5-oxo-5,6-dihydro-2H-pyran-3-olate (Li, Wenke; Wayne, Gregory S.; Lallaman, John E.; Wittenberger, Steven J. J. Org. Chem. (2006), 71, 1725-1727) (1.36 g, 10 mmol) and n-butylthiourea (Trans World) (1.32 g, 10 mmol) in tetrahydrofuran (15 mL) was added a mixture of DMSO/12 N HCl (1/1 molar ratio, 4.6 mL, 30 mmol). The reaction mixture was heated at 40° C. for overnight, and then cooled. The mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic extract was dried (MgSO4), filtered and concentrated. The residue was dried under vacuum for 12 h and dissolved in tetrahydrofuran (40 mL). To the solution was added 5-chloro-2-methoxy-benzoic acid (1.86 g, 10.0 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodimide hydrochloride (1.91 g, 10.0 mmol), 1-hydroxybenzotriazole (1.35 g, 10.0 mmol) and triethylamine (3.5 mL, 3.5 mmol). The mixture was stirred overnight at 80° C. and then cooled at room temperature. The mixture was diluted with ethyl acetate, washed with 1 M aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (SiO2, 0-75% ethyl acetate in hexanes) to afford 412 mg of the title compound. MS (ESI+) m/z 395 (M+H)+ was added cooled washed with aqueous sodium bicarbonate The organic extract was dried (MgSO4) filtered concentrated The residue was dried under vacuum for 12 h dissolved in tetrahydrofuran (40 mL) cooled at room temperature washed with 1 M aqueous NaHCO3 dried (Na2SO4) filtered concentrated The residue was purified by flash chromatography (SiO2, 0-75% ethyl acetate in hexanes)

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of sodium 5-oxo-5,6-dihydro-2H-pyran-3-olate (Wenke et al. J. Org. Chem. 2006, 71, 1725-1727) (1.36 g, 10.0 mmol) and n-butylthiourea (Trans World) (1.32 g, 10.0 mmol) in tetrahydrofuran (15 mL) was added a mixture of DMSO (2.1 mL) and 12 N HCl (2.5 mL). The reaction mixture was heated at 40° C. overnight and cooled. The mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic extract was dried (MgSO4), filtered and concentrated. The residue was dried under vacuum for 12 hours and dissolved in tetrahydrofuran (40 mL). To the solution was added 5-chloro-2-methoxy-benzoic acid (1.86 g, 10.0 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodimide hydrochloride (1.91 g, 10.0 mmol), 1-hydroxybenzotriazole (1.35 g, 10.0 mmol) and triethylamine (3.5 mL, 3.5 mmol). The mixture was stirred overnight at 80° C., then cooled to room temperature. The mixture was diluted with ethyl acetate, washed with 1 M aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography using an Analogix® IT280™ (SiO2, 0-75% ethyl acetate in hexanes) to afford 412 mg of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.03 (t, J=7.46 Hz, 3H) 1.38-1.52 (m, 2H) 1.77-1.90 (m, 2H) 3.93 (s, 3H) 4.16 (t, J=7.46 Hz, 2H) 4.32 (s, 2H) 4.90 (s, 2H) 6.94 (d, J=8.82 Hz, 1H) 7.40 (dd, J=8.99, 2.88 Hz, 1H) 8.11 (d, J=2.71 Hz, 1H); MS (ESI+) m/z 395 (M+H)+. was added cooled washed with aqueous sodium bicarbonate The organic extract was dried (MgSO4) filtered concentrated The residue was dried under vacuum for 12 hours dissolved in tetrahydrofuran (40 mL) cooled to room temperature washed with 1 M aqueous NaHCO3 dried (Na2SO4) filtered concentrated The residue was purified by flash chromatography

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of sodium 5-oxo-5,6-dihydro-2H-pyran-3-olate (Wenke et al. J. Org. Chem. 2006, 71, 1725-1727) (1.36 g, 10.0 mmol) and n-butylthiourea (Trans World) (1.32 g, 10.0 mmol) in tetrahydrofuran (15 mL) was added a mixture of DMSO (2.1 mL) and 12 N HCl (2.5 mL). The reaction mixture was heated at 40° C. overnight and cooled. The mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic extract was dried (MgSO4), filtered and concentrated. The residue was dried under vacuum for 12 hours and dissolved in tetrahydrofuran (40 mL). To the solution was added 5-chloro-2-methoxy-benzoic acid (1.86 g, 10.0 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodimide hydrochloride (1.91 g, 10.0 mmol), 1-hydroxybenzotriazole (1.35 g, 10.0 mmol) and triethylamine (3.5 mL, 3.5 mmol). The mixture was stirred overnight at 80° C., then cooled to room temperature. The mixture was diluted with ethyl acetate, washed with 1 M aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography using an Analogix® IT280™ (SiO2, 0-75% ethyl acetate in hexanes) to afford 412 mg of the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.03 (t, J=7.46 Hz, 3H) 1.38-1.52 (m, 2H) 1.77-1.90 (m, 2H) 3.93 (s, 3H) 4.16 (t, J=7.46 Hz, 2H) 4.32 (s, 2H) 4.90 (s, 2H) 6.94 (d, J=8.82 Hz, 1H) 7.40 (dd, J=8.99, 2.88 Hz, 1H) 8.11 (d, J=2.71 Hz, 1H); MS (ESI+) m/z 395 (M+H)+. was added cooled washed with aqueous sodium bicarbonate The organic extract was dried (MgSO4) filtered concentrated The residue was dried under vacuum for 12 hours dissolved in tetrahydrofuran (40 mL) cooled to room temperature washed with 1 M aqueous NaHCO3 dried (Na2SO4) filtered concentrated The residue was purified by flash chromatography

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of sodium 5-oxo-5,6-dihydro-2H-pyran-3-olate (Li, Wenke; Wayne, Gregory S.; Lallaman, John E.; Wittenberger, Steven J. J. Org. Chem. (2006), 71, 1725-1727) (1.36 g, 10 mmol) and n-butylthiourea (Trans World) (1.32 g, 10 mmol) in tetrahydrofuran (15 mL) was added a mixture of DMSO/12 N HCl (1/1 molar ratio, 4.6 mL, 30 mmol). The reaction mixture was heated at 40° C. for overnight, and then cooled. The mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic extract was dried (MgSO4), filtered and concentrated. The residue was dried under vacuum for 12 h and dissolved in tetrahydrofuran (40 mL). To the solution was added 5-chloro-2-methoxy-benzoic acid (1.86 g, 10.0 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodimide hydrochloride (1.91 g, 10.0 mmol), 1-hydroxybenzotriazole (1.35 g, 10.0 mmol) and triethylamine (3.5 mL, 3.5 mmol). The mixture was stirred overnight at 80° C. and then cooled at room temperature. The mixture was diluted with ethyl acetate, washed with 1 M aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (SiO2, 0-75% ethyl acetate in hexanes) to afford 412 mg of the title compound. MS (ESI+) m/z 395 (M+H)+ was added cooled washed with aqueous sodium bicarbonate The organic extract was dried (MgSO4) filtered concentrated The residue was dried under vacuum for 12 h dissolved in tetrahydrofuran (40 mL) cooled at room temperature washed with 1 M aqueous NaHCO3 dried (Na2SO4) filtered concentrated The residue was purified by flash chromatography (SiO2, 0-75% ethyl acetate in hexanes)

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

实验步骤: N-Butylthiourea is treated with oxalyl chloride to give 1-butyl-2-thioxo-4,5-imidazolidinedione which when substituted for 1-methyl-2-thioxo-4,5-imidazolidinedione in the procedure of Example 1 gives S-[5-(N'-butylthioureido)pentyl]isothiourea.

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of sodium 5-oxo-5,6-dihydro-2H-pyran-3-olate (Li, Wenke; Wayne, Gregory S.; Lallaman, John E.; Wittenberger, Steven J. J. Org. Chem. (2006), 71, 1725-1727) (1.36 g, 10 mmol) and n-butylthiourea (Trans World) (1.32 g, 10 mmol) in tetrahydrofuran (15 mL) was added a mixture of DMSO/12 N HCl (1/1 molar ratio, 4.6 mL, 30 mmol). The reaction mixture was heated at 40° C. for overnight, and then cooled. The mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic extract was dried (MgSO4), filtered and concentrated. The residue was dried under vacuum for 12 h and dissolved in tetrahydrofuran (40 mL). To the solution was added 5-chloro-2-methoxy-benzoic acid (1.86 g, 10.0 mmol), N-(3-dimethylaminopropyl)-N-ethylcarbodimide hydrochloride (1.91 g, 10.0 mmol), 1-hydroxybenzotriazole (1.35 g, 10.0 mmol) and triethylamine (3.5 mL, 3.5 mmol). The mixture was stirred overnight at 80° C. and then cooled at room temperature. The mixture was diluted with ethyl acetate, washed with 1 M aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (SiO2, 0-75% ethyl acetate in hexanes) to afford 412 mg of the title compound. MS (ESI+) m/z 395 (M+H)+ was added cooled washed with aqueous sodium bicarbonate The organic extract was dried (MgSO4) filtered concentrated The residue was dried under vacuum for 12 h dissolved in tetrahydrofuran (40 mL) cooled at room temperature washed with 1 M aqueous NaHCO3 dried (Na2SO4) filtered concentrated The residue was purified by flash chromatography (SiO2, 0-75% ethyl acetate in hexanes)

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

实验步骤: N-Butylthiourea is treated with oxalyl chloride to give 1-butyl-2-thioxo-4,5-imidazolidinedione which when substituted for 1-methyl-2-thioxo-4,5-imidazolidinedione in the procedure of Example 1 gives S-[5-(N'-butylthioureido)pentyl]isothiourea.

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

实验步骤: N-Butylthiourea is treated with oxalyl chloride to give 1-butyl-2-thioxo-4,5-imidazolidinedione which when substituted for 1-methyl-2-thioxo-4,5-imidazolidinedione in the procedure of Example 1 gives S-[5-(N'-butylthioureido)pentyl]isothiourea.

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

实验步骤: 2-Chloro-3-methylquinoxaline (3.572 g., 0.02 mole) was dissolved in 50 ml. of acetone treated with Norit and filtered. The filtrate was added to a solution of 2.645 g. (0.02 mole) n-butylthiourea in 25 ml. acetone. After the mixture was stirred at room temperature for 31/2 hours, the solid which had formed was filtered, washed with acetone, then ether and dried to give 4.86 g. (78.2%) of product as an off-white solid, m.p. 118.5°-119.5°. filtered The filtrate was added to a solution of 2.645 g the solid which had formed was filtered washed with acetone ether and dried to give 4.86 g