nonanenitrile

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:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of octyl cyanide (75.0 g, 0.539 mol), anhydrous zinc acetate (2.47 g, 0.0134 mol) and 1-butanol (270 ml) was stirred at 120° C. under nitrogen. To this mixture was dropwisely added 2-hydroxyethyl amine (39.5 g, 0.647 mol) in 20 min., and the resulting mixture was stirred at 120° C. for 40 h. The resulting admixture was distilled under reduced pressure three times. The fraction at 75°-80° C./0.2 mmHg was collected to give 2-octyl-2-oxazoline as a colorless liquid (46 g, 47% yield). The product was again distilled under reduced pressure from calcium hydride: 1H NMR (CDCl3) delta 0.88 (5, J=6.6 Hz, 3H, CH3), 1.29 (m, 10H, CH2×8), 1.63 (t of t, J=6.6 and 6.9 Hz, 2H, CH2), 2.26 (t, J=7.2 Hz, 2H, CH2), 3.82 (t, J=9.6 Hz, 2H, CH2O), and 4.22 (t, J=9.6, 2H, CH2N). in 20 min. the resulting mixture was stirred at 120° C. for 40 h The resulting admixture was distilled under reduced pressure three times The fraction at 75°-80° C./0.2 mmHg was collected

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: 13.02 g (93.51 mmoles) of octyl cyanide was treated with 12.327 g (118.36 mmoles) of 2-(2-aminoethylamino)ethanol in presence of 0.5 ml of carbon disulfide at 125° C. for 24 hrs. and worked up as outlined under Example 23. Distillation of the residue at 167°-169° C./0.5 mm gave 12.332 g (62.7%) of product. Distillation of the residue at 167°-169° C./0.5 mm

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

実験手順: Octyl cyanide (2 g, 14 mmol) and hydroxylamine hydrochloride (2.495 g, 36 mmol) were dissolved in EtOH (10 mL) and treated with triethylamine (5 mL, 36 mmol) at reflux over night. Extraction: AcOEt/water. Silica gel chromatography: heptane/AcOEt 1:2 afforded a white solid (0.65 g, 26%). MS: m/z=173 (M +H). at reflux over night Extraction

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

実験手順: Octyl cyanide (2 g, 14 mmol) and hydroxylamine hydrochloride (2.495 g, 36 mmol) were dissolved in EtOH (10 mL) and treated with triethylamine (5 mL, 36 mmol) at reflux over night. Extraction: AcOEt/water. Silica gel chromatography: heptane/AcOEt 1:2 afforded a white solid (0.65 g, 26%). MS: m/z=173 (M +H). at reflux over night Extraction

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

実験手順: To a solution of 0.74 g (10.7 mmol) of hydroxylamine hydrochloride in 11 mL of isopropyl alcohol, 1.327 g (17.8 mmol) of sodium bicarbonate was added. The resulting mixture was stirred at 25° C. to 30° C. for 10-15 min. 1.0 g (7.1 mmol) of nonanenitrile was added and stirred at 80° C. to 85° C. for 3-4 h. After the reaction period, the reaction mixture was cooled to 25° C. to 30° C., filtered and washed with 2 mL of isopropyl alcohol. The filtrate was collected and distilled out completely to obtain a crude residue. The residue with chased with 5 mL of toluene below 45° C., under vacuum, to yield the title compound. stirred at 80° C. to 85° C. for 3-4 h After the reaction period the reaction mixture was cooled to 25° C. to 30° C. filtered washed with 2 mL of isopropyl alcohol The filtrate was collected distilled out completely to obtain a crude residue

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of octyl cyanide (75.0 g, 0.539 mol), anhydrous zinc acetate (2.47 g, 0.0134 mol) and 1-butanol (270 ml) was stirred at 120° C. under nitrogen. To this mixture was dropwisely added 2-hydroxyethyl amine (39.5 g, 0.647 mol) in 20 min., and the resulting mixture was stirred at 120° C. for 40 h. The resulting admixture was distilled under reduced pressure three times. The fraction at 75°-80° C./0.2 mmHg was collected to give 2-octyl-2-oxazoline as a colorless liquid (46 g, 47% yield). The product was again distilled under reduced pressure from calcium hydride: 1H NMR (CDCl3) delta 0.88 (5, J=6.6 Hz, 3H, CH3), 1.29 (m, 10H, CH2×8), 1.63 (t of t, J=6.6 and 6.9 Hz, 2H, CH2), 2.26 (t, J=7.2 Hz, 2H, CH2), 3.82 (t, J=9.6 Hz, 2H, CH2O), and 4.22 (t, J=9.6, 2H, CH2N). in 20 min. the resulting mixture was stirred at 120° C. for 40 h The resulting admixture was distilled under reduced pressure three times The fraction at 75°-80° C./0.2 mmHg was collected

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: Octyl cyanide (2 g, 14 mmol) and hydroxylamine hydrochloride (2.495 g, 36 mmol) were dissolved in EtOH (10 mL) and treated with triethylamine (5 mL, 36 mmol) at reflux over night. Extraction: AcOEt/water. Silica gel chromatography: heptane/AcOEt 1:2 afforded a white solid (0.65 g, 26%). MS: m/z=173 (M +H). at reflux over night Extraction

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

実験手順: A Grignard solution of 2-ethylhexylmagnesiumbromide in diethylether (1.0 M, 110 mL, 0.11 mol) was slowly added via syringe to a stirred mixture of n-octylcyanide (4.66 g, 55 mmol) in diethyl ether (100 mL) at 0° C. under N2 atmosphere. After stirring for 12 h at reflux temperature, the reaction was quenched with an aqueous HCl-solution (2.0 M, 50 mL) at 0° C. and subsequently vigorously stirred for an additional 3 h at room temperature. The organic phase was separated and the aqueous phase was extracted with diethylether. The combined organic phases were washed with a saturated bicarbonate solution and brine, dried over MgSO4 and evaporated under reduced pressure to give a yellow solid. The resulting solid was purified by recrystallization from acetone to afford white crystals (IX) (4.51 g, 32%). 1H-NMR (CDCl3): δ=2.99-2.79 (m, 4H), 2.64-2.50 (m, 1H), 1.82-1.55 (m, 4H), 1.57-1.03 (m, 18H), 0.89-0.71 (m, 9H). 13C-NMR (CDCl3): δ=164.35, 34.89, 32.44, 30.31, 30.09, 29.90, 29.79, 28.48, 28.31, 25.71, 23.26, 14.71. at reflux temperature the reaction was quenched with an aqueous HCl-solution (2.0 M, 50 mL) at 0° C. subsequently vigorously stirred for an additional 3 h at room temperature The organic phase was separated the aqueous phase was extracted with diethylether The combined organic phases were washed with a saturated bicarbonate solution and brine dried over MgSO4 evaporated under reduced pressure to give a yellow solid The resulting solid was purified by recrystallization from acetone