In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N-Butyl-2-cyano-acetamide, other downstream synthetic routes, hurry up and to see.
Synthetic Route of 39581-21-0, The chemical industry reduces the impact on the environment during synthesis 39581-21-0, name is N-Butyl-2-cyano-acetamide, I believe this compound will play a more active role in future production and life.
Example 11. Synthesis of 1,5-dibutyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (AA11) [Show Image] Under the nitrogen gas atomosphere, a mixture of 28% sodium methoxide methanol solution (39 mL, 202 mmol) and ether (260 mL) was cooled to 3C in an ice bath, and the mixture of 2-heptanone (22.84 g, 200 mmol) and ethyl formate (16.15 g, 218 mmol) was dropped in about 20 minutes. After that, being stirred at the same temperature for 30 minutes, then the mixture was returned to be at room temperature and was further stirred for 20 hours afterwards. The precipitated product was removed by filtration and washed enough with ether (about 620 g). The mother liquor and the washing layer were combined and concentrated to give a crude product of 29.34 g. This crude product was repeatedly washed with hexane and ether, and powdered yellow ocher sodium salt of 3-[1-hydroxymethylidyne]-heptan-2-one (11.33 g, 34.5%) was obtained. This salt (2.13 g, 13 mmol) was suspended in DMF (10 mL), and n-butylcyanoacetamide (1.40 g, 10mmol), acetic acid (0.75 mL, 13.1 mmol), piperidine (0.20 mL, 2.02 mmol) were added in order at room temperature, and the mixture was refluxed at 135C for 7 hours. After that, the reaction mixture was let alone at room temperature for 13 hours and then poured into ice water, and the obtained mixture was extracted with ethyl acetate two times. The organic layer was washed with diluted hydrochloric acid one time and with water two times, and then died with anhydrous magnesium sulfare. The solvent was removed by distillation under reduced pressure, and a red oily crude product of 2.03 g was obtained. This crude product was refined by the silica gel chromatography, and the desired 1, 5-dibutyl-6-methyl-2-oxo-1, 2-dihydropyridine-3-carbonitrile (AA11, 420 mg, 17.3%) and 1-butyl-2-oxo-6-pentyl-1,2-dihydropyridine-3-carbonitrile (230 mg, 9.4%) were obtained. AA11 NMR:(CDC13) 0.95 (t, 3H, J=6.9, 0.98 (t, 3H, J=6.9), 1:5-1.7 (m, 8H), 2.42 (s, 3H), ca 2.4 (m, 2H), 4.08 (2H, m), 7.57 (1H, s)) 1-butyl-2-oxo-6-pentyl-1,2-dihydropyridine-3-carbonitrile NMR: (CDCl3) 0.94 (t, 3H, J=6.8), 0.98 (t, 3H, J=7.2), 1.3-1.7 (m, 10H), 2.66 (m, 2H), 4.04 (m, 2H), 6.11 (ABd, 1H, J=7.5), 7.67 (ABd, 1H, J=7.5)) was obtained.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N-Butyl-2-cyano-acetamide, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; SHIONOGI & CO., LTD.; EP1806342; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts