6-azidohexanoyl chloride

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent

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

実験手順: The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] as follows: To 6-azidohexanoic acid (7.5 g, 47.7 mmol) previously cooled to 0° C. was added 10 ml (16.3 g, 137 mmol) of thionyl chloride and the solution was stirred in cold until the evolution of gas had subsided (5-10 min) and then refluxed for 1 h. The reaction mixture was evaporated and the residue distilled to give 5.5 g (65.6%) of title compound bp 110°-111° C./12 Tor (lit. bp 73°-75° C./0.1 torr); ir (neat) νmax : 2097 (N3), 1795 cm-1 (C=O); 1Hmr (CDCl3) δ: 1.1-2.0 (m, 6H, 3CH2), 2.9 (m, 2H, CH2CO), 3.27 (m, 2H, CH2N 3). The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] (5-10 min) refluxed for 1 h The reaction mixture was evaporated the residue distilled

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (6.31 g, 43.8 mmol) and 4-dimethylaminopyridine (5.60 g, 45.9 mmol) in 100 ml of CH2Cl2 was added dropwise a solution of crude 6-azidohexanoic chloride (7.32 g, 41.7 mmol) in 30 ml of CH2Cl2 at 0° C. The mixture was stirred at 0° C. for 1 hr then at room temperature for 1 hr. The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) followed by brine (100 ml) and dried over Na2SO4. After filtration and evaporation of solvent, 5-(6-azidohexanoyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was obtained as a light red oil (12.0 g, 100%). at room temperature for 1 hr The solution was washed with 0.5N aqueous HCl (100 ml), water (100 ml) dried over Na2SO4 After filtration and evaporation of solvent

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

実験手順: The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] as follows: To 6-azidohexanoic acid (7.5 g, 47.7 mmol) previously cooled to 0° C. was added 10 ml (16.3 g, 137 mmol) of thionyl chloride and the solution was stirred in cold until the evolution of gas had subsided (5-10 min) and then refluxed for 1 h. The reaction mixture was evaporated and the residue distilled to give 5.5 g (65.6%) of title compound bp 110°-111° C./12 Tor (lit. bp 73°-75° C./0.1 torr); ir (neat) νmax : 2097 (N3), 1795 cm-1 (C=O); 1Hmr (CDCl3) δ: 1.1-2.0 (m, 6H, 3CH2), 2.9 (m, 2H, CH2CO), 3.27 (m, 2H, CH2N 3). The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] (5-10 min) refluxed for 1 h The reaction mixture was evaporated the residue distilled

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

実験手順: The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] as follows: To 6-azidohexanoic acid (7.5 g, 47.7 mmol) previously cooled to 0° C. was added 10 ml (16.3 g, 137 mmol) of thionyl chloride and the solution was stirred in cold until the evolution of gas had subsided (5-10 min) and then refluxed for 1 h. The reaction mixture was evaporated and the residue distilled to give 5.5 g (65.6%) of title compound bp 110°-111° C./12 Tor (lit. bp 73°-75° C./0.1 torr); ir (neat) νmax : 2097 (N3), 1795 cm-1 (C=O); 1Hmr (CDCl3) δ: 1.1-2.0 (m, 6H, 3CH2), 2.9 (m, 2H, CH2CO), 3.27 (m, 2H, CH2N 3). The above compound was prepared by a literature procedure [V. M. Rothe and K. Gehrke, Makromol Chem. 83, 1 (1965)] (5-10 min) refluxed for 1 h The reaction mixture was evaporated the residue distilled