3-Thiophenecarbonitrile

Clear colorless liquid

General procedure: A round bottom flask was charged with a mixture of benzaldehyde 1(1.0 mmol), NH2OH.HCl 2 (1.5 mmol), Cog-C3N4 (20 mg) in H2O/MeOH (1:1, 5 mL) and stirred under the visible light condition at roomtemperature for 14–20 h. After completion of the reaction (monitored by TLC), the catalyst was filtered and added EtOAc (10 mL). Remaining organic layer was washed with brine (2×5 mL) and distilled water(1×10 mL) and dried over anhydrous sodium sulfate. Solvent was evaporated under reduced pressure to afford the crude residue, which was further purified by flash chromatography, EtOAc/n-hexane: 10:90 to obtain the analytically pure product 3General procedure for the synthesis of nitriles: A pressure tube was charged with an appropriate amount of Zn(OTf)General procedure: Benzyl alcohol was added in a 2L round-bottomed flask (108.02g, 1000mmol, i.e., of formula (I) wherein R is H, X = C, n = 1, m = 0), cuprous iodide (9.50g, 50mmol) , of N- phenylglycine (7.51g, 50mmol), TEMPO ( 7.80g, 50mmol), sodium carbonate (10.60g, 100mmol), aqueous ammonia (300mL, 25 ~ 28percent) , 800mL methanol, under ice-cooling, with the oxygen round bottom flask was evacuated of air ventilation 3 times, and then the system was stirred at 50 at 12h, after completion of the reaction, the reaction solution was cooled to room temperature, the solvent was distilled off under reduced pressure and dried to give the product benzonitrile 95.79g, yield 93percent. The reactants used is 2-thiophene methanol (57.12g, 500mmol, i.e., of formula (I) wherein R is H, X = S, n = 0, m = 0), experimental methods and procedures were the same as in Example 1, except that: cuprous iodide (4.76g, 25mmol), N- phenylglycine (3.79g, 25mmol), TEMPO ( 3.91g, 25mmol), sodium hydroxide (2.03g, 50mmol), aqueous ammonia (60mL, 25 ~ 28percent), methanol 160mL, stirred at at 50 24h, to give the final product 49.05g, yield 90percent.General procedure: PdClGeneral procedure: Following the amide intermediate Preparation Example A. The reaction vessel is closed (when the amide intermediate has a boiling point at normal pressure equal to or lower than the reaction temperature TB described below) or the reaction vessel is kept open (when the amide intermediate has a boiling point higher than the normal pressure When the reaction temperature is TB), the stirring is continued (600 r/min), the reaction temperature is changed to TB, and after the reaction temperature TB is maintained for TD hours, the reaction is almost complete. Then, the reaction vessel was sealed and connected to a vacuum pump so that the degree of vacuum in the reaction vessel reached 20-50 mbar (according to the type of nitrile product) and the distillate was used as the nitrile product. The yield of the nitrile product was calculated and sampled for nuclear magnetic proteomics and elemental analysis to characterize the nitrile product obtained. Specific reaction conditions and characterization results are shown in Tables A-7, A-8, A-9, A-10 and A-11 below. These characterization results show that the nitrile product obtained has an extremely high purity (above 99percent).In these nitrile product preparation examples, 10 g of diphosphorus pentoxide was optionally added to the reaction vessel as a catalyst at the start of the reaction.

Molecular Weight:109.15
XLogP3:1.3
Hydrogen Bond Acceptor Count:2
Exact Mass:108.99862027
Monoisotopic Mass:108.99862027
Topological Polar Surface Area:52
Heavy Atom Count:7
Complexity:102
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes