* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With copper diacetate; acetonitrile In ethanol at 78℃; for 5 h;
General procedure: To a 25 mL round-bottom flask equipped with a magnetic stirrer were added aldoximes (5 mmol), copper(II) acetate (45 mg, 0.25 mmol),acetonitrile (10 mg, 0.25 mmol) and EtOH (15 mL). The mixture was stirred for 4–8 h at 78 °C or for 12 h at room temperature. After removal of the solvent, the residue was purified by column chromatography to afford the desired product.
Reference：
[1] RSC Advances, 2016, vol. 6, # 43, p. 37093 - 37098
[2] Journal of Chemical Research, 2016, vol. 40, # 10, p. 594 - 596
[3] Bulletin de la Societe Chimique de France, 1967, p. 4115 - 4120
2
[ 18791-75-8 ]
[ 83933-17-9 ]
Yield
Reaction Conditions
Operation in experiment
98%
With hydroxylamine hydrochloride; caesium carbonate In water; dimethyl sulfoxide at 125℃; for 14 h;
General procedure: Aldehyde (0.5mmol), NH2OH·HCl (0.6mmol) and Cs2CO3 (0.6mmol) were stirred at 125°C for 48h in a 3:1 mixture of DMSO–H2O (2mL) under air. The progress of the reaction was monitored by TLC using ethyl acetate and hexane as eluent. After completion, the reaction mixture was cooled to room temperature and treated with water (1mL). The resulting mixture was extracted with ethyl acetate (3×5mL). Drying (Na2SO4) and evaporation of the solvent gave a residue that was purified on silica gel column chromatography using ethyl acetate and hexane. The purified products were identified by 1H NMR spectra and the melting points comparison with the literature data.
Stage #1: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2 h; Stage #2: With ammonia In water; N,N-dimethyl-formamide at 0 - 20℃; for 5 h;
A solution of 4 bromo-thiophene-2-carbo xylic acid (2.Og, 9.66mmol), l-ethyl-3-(3'- dimethylaminopropyl)carbodiimide hydrochloride (2.04g, 10.63mmol) and 1 -hydroxybenzotriazole hydrate (1.44g, 10.63mmol) in DMF (2OmL) is stirred at room temperature for 2 hours. The reaction mixture is then cooled to O0C and aq. NH3 (ImL, 17.3mmol) is added. The mixture is stirred at room temperature for an additional 5 hours, then water is added to the reaction mixture and the resultant precipitate is collected by filtration and washed with IM NaOH, H2O and petroleum ether. The title compound is isolated as a white solid (1.56g, 78percent).
8 g
With N-hydroxybenzotriazole ammonium salt; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In acetonitrile
A) 4-bromothiophene-2-carboxamide [0504] To a solution of 4-bromothiophene-2-carboxylic acid (15 g), HOBt ammonium salt (16.5 g) and triethylamine (20.08 mL) in acetonitrile (250 mL) was added EDCI hydrochloride (16.87 g), and the mixture was stirred overnight. The reaction mixture was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8.0 g). 1H NMR (300 MHz, CDCl3) δ 5.87 (2H, brs), 7.43 (2H, q, J = 1.4 Hz)
Reflux 4-bromo-2-fhiophenecarboxylic acid (960 mg, 4.63 mmol) in SOCl2 (5 mL) for Ih. Evaporate excess SOCl2. Add THF (5 mL) to the residue. Slowly drop the resulting solution to cone NH4OH (15 mL) in ice bath. Stir the mixture overnight. Concentrate the mixture, followed by addition of EtOAc, wash with brine; and dry over MgSO4; filter and concentrate in vacuo. Add NaCl (307 mg, 5.26 mmol) and dichloromethane (10 mL) to the residue and reflux for 30 min. After the addition OfPOCl3 (3.36 g, 21.9 mmol), reflux the mixture for 1 h. Dilute the mixture with dichloromethane and wash with aqueous NaHCO3 solution, brine and dry over MgSO4; filter and concentrate in vacuo to provide 753 mg of the desired product.
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