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CAS No. : | 2947-61-7 | MDL No. : | MFCD00001922 |
Formula : | C9H9N | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RNHKXHKUKJXLAU-UHFFFAOYSA-N |
M.W : | 131.17 | Pubchem ID : | 76280 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 40.93 |
TPSA : | 23.79 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.91 cm/s |
Log Po/w (iLOGP) : | 1.77 |
Log Po/w (XLOGP3) : | 1.67 |
Log Po/w (WLOGP) : | 2.06 |
Log Po/w (MLOGP) : | 2.1 |
Log Po/w (SILICOS-IT) : | 2.61 |
Consensus Log Po/w : | 2.04 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.08 |
Solubility : | 1.08 mg/ml ; 0.00825 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.78 |
Solubility : | 2.16 mg/ml ; 0.0165 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.24 |
Solubility : | 0.0757 mg/ml ; 0.000577 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 1.2h; Green chemistry; | General procedure for the synthesis of carboxylic acids from nitriles General procedure: Aromatic or aliphatic nitriles (2 mmol) were dissolved in 5 ml of [bmim]HSO4 and the reaction mixture was heated at 60-65 °C for 1-3 h. The progress of reaction was monitored by TLC. After completion of reaction, as checked by TLC, the reaction mixture was poured into water containing crushed ice. The product was precipitated out, filtered and dried. The yield of the final product was high (>90%) in all cases. All final products obtained were found sufficiently pure so it didn’t need further purification.The filtrate was concentrated under vacuum, washed with diethylether twice and concentrated under high vacuum. After proper drying under reduced pressure, approximately 95% ionic liquid was recovered from the reaction and compared with the original ionic liquid to check its authenticity. The efficiency of recovered ionic liquid in conversion of nitriles to acids was found unchanged in comparison to the original one and we reused it up to 5-6 cycles without any significant loss of its activity. |
82.6% | With potassium phosphate buffer at 30℃; for 19h; Rhodococcus sp. AJ270 cells; | |
With sulfuric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With [RuCl2(1,3,5-triaza-7-phosphaadamantane)4]; lithium hydroxide monohydrate at 100℃; for 7h; Green chemistry; | 1.3 The ability to store aqueous solutions of [RuCl2(PTA)4] prompted exploring the reusability of the catalyst through recycling experiments with benzonitrile and 4-methylbenzyl cyanide (See Table 5 below). After 7 hours, the reaction was cooled overnight and the aqueous supernatant containing the catalyst was carefully transferred to another reaction tube followed by addition of fresh nitrile. The precipitated amide product was collected and washed with cold water. Further purification was unnecessary as determined by GC-MS, 1H and 13C{1H} NMR spectroscopy. The isolated yields in Table 5 below were obtained by decantation; maximized isolated yields (93%) can be obtained by extraction with an organic solvent (Table 5, run 1c). Recycling was carried out at least seven times without significant loss of the catalytic activity or selectivity in the case of benzonitrile. With 4-methylbenzyl cyanide a decrease in activity was observed after the fifth recycling experiment. This is attributed to incomplete catalyst recovery during transfer of the aqueous supernatant indicated by a faint yellow color observed in the product. The fine solid product made complete transfer of the aqueous catalyst supernatant difficult, resulting in the lower conversion.The isolated yields in the aqueous phase recycling experiments with benzonitrile were modest as decantation left some benzamide dispersed in water. Aqueous/organic biphasic hydration of benzonitrile was thus also studied (See Table 6 below). Due to the mixing efficiency of two phases, aqueous biphasic hydration of benzonitrile to benzamide reached 84% conversion after 7 hours compared to 99% conversion in water; therefore, 24 hours was used in the biphasic reactions. After 24 hours the organic phase (tert-amyl alcohol) was decanted off and benzamide isolated. Fresh benzonitrile and tert-amyl alcohol were added to the aqueous phase for the next reaction. The catalyst could be recycled five times without significant loss of catalytic activity. A slight decrease in catalytic activity was observed after the fifth cycle attributed to catalyst leaching into the organic layer (slight yellow color observed over time in the organic layer). Ruthenium leaching into the organic layer was indeed observed by ICP-AES with the [Ru] increasing with each cycle: recycling experiment 1 (2.9 ppm Ru), 4 (24.5 ppm Ru), and 7 (77.2 ppm Ru). |
87% | With carbon dioxide; tetrabutylphosphonium 2-hydroxypyridine; lithium hydroxide monohydrate at 100℃; for 12h; Sealed tube; | |
85% | With lithium hydroxide monohydrate; [RuCl2(dmso)3(NH3)]PF6Cl at 60℃; for 24h; |
81% | With [RuCl2(PTA)4]; lithium hydroxide monohydrate at 100℃; for 7h; | |
81% | With [(η6-toluene)RuCl(κ2-(P,N)-(1,3,5-triaza-7-phosphaadamantan-6-yl)CPh2NHPh)]Cl; lithium hydroxide monohydrate at 100℃; for 7h; | |
81% | With lithium hydroxide monohydrate; N,N,N-trimethyl-2-hydroxyethyl-ammonium hydroxide at 80℃; for 2h; Green chemistry; | |
72% | With lithium hydroxide monohydrate; N-ethyl-N,N-diisopropylamine; Eosin at 20℃; for 24h; Irradiation; Green chemistry; | |
67% | With Os(H)6(P(i)Pr3)2; lithium hydroxide monohydrate In tetrahydrofuran-d8 at 100℃; for 24h; Inert atmosphere; | |
With hydrogenchloride at 50℃; | ||
With potassium hydroxide; dihydrogen peroxide | ||
With C40H45ClN3O2PRu In methanol; lithium hydroxide monohydrate at 20℃; for 4h; Inert atmosphere; Schlenk technique; Green chemistry; | 4.7. General procedure for the hydration of nitriles to amides General procedure: Organic nitrile (1 mmol) and distilled water (1 mL) were sequentially added to 3 mL methanol solution of the [Ru-NHC] catalyst (0.5 mol%) and the reaction mixture was stirred at room temperature. The progress of the reaction in each case was monitored by TLC analysis. After completion of reaction the catalyst was extracted from the reaction mixture by the addition of CH2Cl2/petroleum ether followed by filtration. The filtrate was subjected to GC analysis and the product was identified with authentic samples. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: (4-methylphenyl)acetonitrile With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 10℃; for 0.166667h; Stage #2: 1-benzoyl-1H-benzotriazole In dimethyl sulfoxide at 25℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | Stage #1: (4-methylphenyl)acetonitrile With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: 3-chloro-6-phenylpyradazine In dimethyl sulfoxide at 50℃; for 12h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 46 percent / NaH / dimethylsulfoxide 2: 69 percent / KOH / bis-(2-hydroxy-ethyl) ether | ||
Multi-step reaction with 2 steps 1: potassium hydroxide / dimethyl sulfoxide / 12 h / 20 °C 2: potassium hydroxide / ethylene glycol; water / 24 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 65 percent / CH3ONa / methanol / 5 h / Ambient temperature 2: dimethylformamide / 2 h / Ambient temperature 3: 1.) CH3ONa / 1.) CH3OH, 30 min, 10 deg C, 2.) CH3OH, reflux, 6 h | ||
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere 2.2: 40 °C / Inert atmosphere 3.1: sodium methylate / methanol / 65 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran / 20 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: sodium methylate / methanol / 65 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64.2% | With 1,8-diazabicyclo[5.4.0]undec-7-ene In nitrogen | 14.1 (1) (1) Synthesis of 2-(p-tolyl)-2-(2'-piperidinylidene) acetonitrile (4d) Into a 30 ml eggplant type flask were charged 1 g (8.84 mmol) of 2,3,4,5-tetrahydro-6-methoxypyridine, 1.10 ml (8.84 mmol) of p-methylphenylacetonitrile and 132 μl (0.84 mmol) of DBU. The reaction mixture was then heated to a temperature of 150° C. in a nitrogen stream for 40 hours. The reaction mixture was then allowed to cool to room temperature. The reaction mixture was then concentrated under reduced pressure by an evaporator. The resulting residue was then purified through silica gel column chromatography (6:1 by volume mixture of hexane and ethyl acetate) to obtain 1.20 g (yield: 64.2%) of 2-(p-tolyl)-2-(2'-piperidinylidene)acetonitrile in the form of white crystal. The product thus obtained exhibited the following physical properties. 1 H-NMR (CDCl3 /Me4 Si) δ: 1.64 (m, 0.56 H), 1.78 (m, 3.44H), 2.32, 2.34 (s, 3H), 2.47 (t, J=0.39H), 2.78 (m, 1.61H), 3.16 (m, 1.61H), 3.34 (0.39H), 5.39 (br, 1H), 7.11-7.26 (m, 4H) 13 C-NMR (CDCl3 /Me4 Si) δ: 20.98, 21.13, 21.71, 21.79, 23.51, 27.20, 28.61, 43.08, 43.41, 123.30, 129.45, 129.75, 129.98, 130.68, 131.12, 136.41, 137.30, 157.77, 160.05 MS: 212 (M+), 197, 183, 169, 155, 140, 129, 91, 82, 43 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium chloride In water; dimethyl sulfoxide | 16.A 2-n-Butyl-4-spirocyclopentane-1-[4-(1-(5-tetrazolyl)cyclohexyl)benzyl]-2-imidazolin-5-one. STR35 A) 1-Cyano-1-(para-tolyl)cyclohexane. This compound is prepared according to the operating procedure described in J. Org. Chem. 1971, 36 (9), 1308. 2.7 g of 80% sodium hydride in oil are placed, under argon, in 40 ml of DMSO and a mixture of 5.24 g of para-methylbenzyl cyanide and 10.12 g of 1,5-dibromopentane in 20 ml of ether is added dropwise while maintaining the temperature between 25° and 35° C. using a bath of cold water. After the end of the exothermic reaction, the mixture is left stirring for 1 hour at 25° C. and is then cooled in an ice bath. 3 ml of isopropyl alcohol and 30 ml of water are added. After separation, extraction is carried out with ether and AcOEt. The organic phases are combined and washed 3 times with water and then with a saturated solution of sodium chloride, they are then dried over sodium sulphate and evaporated. The product is then distilled under reduced pressure (0.2 mm Hg): BP=98°-102° C. 4.2 g of the pure product are obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium iodide; In N-methyl-acetamide; | 76.1 Synthesis of 1-benzyl-4-(4-methyl-phenyl)-4-cyano-piperidine 4-Methylphenyl-acetonitrile (1.66 g, 12.6 mmol), sodium iodide (0.25 g), and sodium hydride (50.4 mmol) were combined in dimethylformamide (50 mL) and stirred until gas evolution ceases. A solution of <strong>[10429-82-0]N,N-bis(2-chloroethyl)-N-benzylamine hydrochloride</strong> (2.8 g, 12.6 mmol) in dimethylformamide (50 mL) was added dropwise. After 24 hours, the reaction mixture was heated to 70 C. and stirred for 2 days. The solvent was removed by evaporation in vacuo to give a residue and the residue was partitioned between water and dichloromethane. The organic layer was separated, dried over MgSO4, filtered and evaporated in vacuo to give a residue which was chromatographed on silica gel eluding with 2/1 hexane/ethyl acetate to give the title compound. | |
With sodium iodide; In N-methyl-acetamide; | 76.1 Synthesis of 1-benzyl-4-(4-methyl-phenyl)-4-cyano-piperidine 4-Methyl-phenyl-acetonitrile (1.66 g, 12.6 mmol), sodium iodide (0.25 g), and sodium hydride (50.4 mmol) were combined in dimethylformamide (50 mL) and stirred until gas evolution ceases. A solution of <strong>[10429-82-0]N,N-bis(2-chloroethyl)-N-benzylamine hydrochloride</strong> (2.8 g, 12.6 mmol) in dimethylformamide (50 mL) was added dropwise. After 24 hours, the reaction mixture was heated to 70 C. and stirred for 2 days. The solvent was removed by evaporation in vacuo to give a residue and the residue was partitioned between water and dichloromethane. The organic layer was separated, dried over MgSO4, filtered and evaporated in vacuo to give a residue which was chromatographed on silica gel eluding with 2/1 hexane/ethyl acetate to give the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid at 110℃; for 3h; | 57.A EXAMPLE 57; A^-{(35)-145-(4-methylbenzyl)-l,3,4-thiadiazol-2-yl]pyrrolidin-3-yl}-l/f-pyrazolo[3,4- |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
zinc(II) chloride; In diethyl ether; | EXAMPLE 1 <strong>[533-73-3]1,2,4-Trihydroxybenzene</strong> (40.3 g) is suspended in dry diethylether (250 ml) containing dry ZnCl2 (38.2 g) and 4-methylphenylacetonitrile (49.8 g). The suspension is then exposed for 6 h at 0 to a gentle stream of dry HCl, te gas bubbling through the suspension under continuous stirring. Then the reaction mixture is kept for 50 h at 4 and thereafter the supernatant is decanted from heavy oil which is separated. The oil is washed twice with diethylether, then with water (1 l), and conc. HCl (20 ml) are added and the mixture is boiled for 1 h under reflux. After cooling to room temperature, the mixture is extracted with diethylether (3*250 ml). The combined ether solutions are extracted with NaOH 2N solutions (3*100 ml). The alkali extract is acidified with conc. HCl and the mixture cooled on ice. The crude product is filtered off and recrystallized from methanol/water. The product is dried in vacuo to constant weight to yield 2,4,5-trihydroxyphenyl-4'-methylbenzylketone, m.p. 173. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.2 g | Multistep reaction.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | 4-Methyl-benzyl nitrile (23g, 0.17 mol) and and 4-chloro-2-fluoro-benzene nitrile (23g, 0.16 mol) were added at room temperature to a solution of potassium tert-butoxide (37g, 0. 33mol) in DMF (250 mL). The mixture was stirred for 45 minutes before chloroacetate methyl ester (20 ML) was added dropwise. The reaction was stirred for 4 hours at ambient temperature and then poured onto ice. The title product crystallised and was filtered and then washed with water and ether. Yield 34g, 64%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With caesium carbonate In dimethyl sulfoxide at 130 - 140℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With potassium hydroxide; In methanol; at 20℃; for 24h; | General procedure: To a solution of KOH (13.3 g, 238 mmol) in methanol (50mL) the appropriate 1-alkyl-5-nitro-1H-indazoles (10 mmol) and arylacetonitrile (12 mmol) were added with stirring. The mixture was stirred at rt for 24 h. After concentration at reduced pressure, the precipitate was collected by filtration, washed with water, following with EtOH, and then air dried to give crude 3a-e and 4a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With potassium hydroxide In methanol at 20℃; for 24h; | |
63% | With potassium hydroxide In methanol at 20℃; for 24h; | General Procedure for the Synthesis of 3a-e and 4a-d. General procedure: To a solution of KOH (13.3 g, 238 mmol) in methanol (50mL) the appropriate 1-alkyl-5-nitro-1H-indazoles (10 mmol) and arylacetonitrile (12 mmol) were added with stirring. The mixture was stirred at rt for 24 h. After concentration at reduced pressure, the precipitate was collected by filtration, washed with water, following with EtOH, and then air dried to give crude 3a-e and 4a-d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / 1 h / Reflux 2: acetic acid; hydrazine hydrate / ethanol / 1 h / 80 - 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With tert.-butylhydroperoxide; copper(l) iodide In N,N-dimethyl acetamide; water at 130℃; for 20h; | 2. General procedure for the synthesis of 3 General procedure: Boronic acid 1 (0.5mmol), benzyl cyanide 2 (0.75mmol), CuI (95mg, 0.5mmol), tert-BuOOH (70% aq, 144μL, 1mmol), and DMAc (2mL) were placed in a 25mL round flask. The reaction mixture was stirred at 130°C (oil bath) for 20h under air. After cooling to the room temperature, the resulting mixture was poured to 15mL water and extracted with dichloromethane (3×5mL). The organic phase was combined and dried over anhydrous Na2SO4. Dichloromethane was evaporated under reduced pressure and the residue was purified by flash column chromatography on a silica gel to give the product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hexamethyldisilazane Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With [2,2]bipyridinyl; palladium diacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 36h; Schlenk technique; Inert atmosphere; | Alkyl Aryl Ketones 3 and 2-Arylbenzofurans 4; General Procedure General procedure: To a Schlenk tube with a magnetic stirring bar were charged the respective nitrile 1 (0.4 mmol), arylboronic acid 2 (0.8 mmol), Pd(OAc)2 (5 mol%), bpy (10 mol%), TFA (10 equiv), THF (2 mL), and H2O (0.4 mL) under N2 atmosphere. The reaction mixture was stirred at 80 °C for 36 h. After cooling to r.t., the mixture was poured into EtOAc (5 mL), which was washed with sat. aq NaHCO3 (2*10 mL) and then brine (1*10 mL). After extracting the aqueous layer with EtOAc (3*10 mL), the combined organic layers were dried (Na2SO4), and evaporated under vacuum. The residue was purified by flash column chromatography (hexane-EtOAc) to afford the desired products 3 or 4. All known compounds afforded analytical data identical to those reported literature previously (see Supporting Information for further details). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With potassium hydroxide; In methanol; for 2h;Reflux; | General procedure: To a solution of KOH (20 g, 357 mmol) in methanol (80 mL) compounds 1a-d (10 mmol) and 2a-c (12 mmol) were added with stirring. The mixture was refluxed with stirring for 2 h, and then poured into water and then it was neutralized with dilute HCl solution. The precipitate was collected by filtration, washed with water, following with n-hexane-dichloromethane (50:50), and then air dried to give practically pure 3a-f. More purification was achieved by crystallization from suitable solvent such as n-hexane-ethyl acetate or acetone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With oxygen; copper dichloride In toluene at 110℃; for 48h; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium hydroxide In methanol for 3h; Reflux; | Synthesis of compounds 3a-c General procedure: Compounds 1 (5 mmol) and 2a-c (7 mmol) were added with stirring to a solution of KOH (10 g, 0.18 mol) in methanol (50 ml). The mixture was refluxed for 3 h with stirring and then poured into water. After neutralization with dilute HCl solution, the precipitate was filtered off, washed with water, followed by EtOH and acetone, and then air-dried to give products 3a-c. High purity (99.9%) was achieved by crystallization from pyridine. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58%Chromat. | With copper(I) oxide; copper(l) iodide; In 1-methyl-pyrrolidin-2-one; | Example 12 In 10ml reaction flask was added 0.25mmol cuprous iodide, 0.25mmol cuprous oxide , 1mmol 3-nitro-4-chloro-trifluoromethylbenzene, 1.2mmol of p-methylbenzylcyanide, 2ml N-methylpyrrolidone, air stirring heated to 160C , 18 hours after the reaction is stopped. Taking 50 microliters reaction liquid water and methylene chloride extraction extracting the organic phase to gas chromatographic analysis, the results show the reaction yield is 58%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium hydroxide In acetonitrile at 60℃; for 1.5h; | General procedure for synthesis of 6a. General procedure: To 20 mL colorimetrictube was added 4a (147.1 mg, 1.0 mmol), 5a (270.3 mg,3.0 mmol), AgMnO2 (10 mg), KOH (168.3 mg, 3.0 mmol),and CH3CN (3.0 mL). The mixture was stirred at 60 °C for1.5 h and then cooled to room temperature. After removingthe solvent, the resulting reside was directly purified by columnchromatography with petroleum ether/ethyl acetate aseluent to give the desired product. |
90% | With Zr6(μ3-O)4(μ3-OH)4(OH)6(H2O)6(IDA)3; potassium hydroxide In acetonitrile at 80℃; for 10h; | |
81% | In water; acetonitrile at 60℃; for 16h; Molecular sieve; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.2% | With 1,4-diaza-bicyclo[2.2.2]octane; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); trimethylphosphine(hexafluoroacetylacetonato)copper(I); 1-butyl-3-methylimidazolium trifluoromethanesulfonimide salt; silver trifluoromethanesulfonate In ethylene glycol; dimethyl sulfoxide at 80℃; for 4h; Inert atmosphere; | 1 At room temperature, the appropriate amount of organic solvent (DMSO and ethylene glycol as a mixture of equal volume), and (I) compound, 100mmol formula (II) compounds of the formula 100mmol, 12mmol catalyst (as 9.6mmol (A-taPhos)2PdCl2And a mixture of 2.4mmol trimethylphosphine (hexafluoroacetylacetonato) copper), 140mmol oxidant silver trifluoroacetate, 200mmol 10mmol base DABCO accelerator and 1-butyl-3-methylimidazolium trifluoromethane sulfonimide salt and then replaced with nitrogen several times, until the reaction atmosphere is a nitrogen atmosphere; temperature was elevated to 80 deg.] C, and stirred at this temperature for 4 hours; After completion of the reaction, the reaction solution was allowed to cool to room temperature, filtered, adjusted to neutral pH of the filtrate, water was sufficiently washed with saturated brine, and then ethyl acetate was added and extracted 3 times, the organic phases combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, the resulting residue was purified by column chromatography over silica gel 300-400 mesh, in a volume ratio of 1: 2 mixture of methylene chloride and acetone, elution was carried out to afford the compound of formula (III), in a yield of 96.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With potassium <i>tert</i>-butylate In dimethyl sulfoxide; <i>tert</i>-butyl alcohol at 80℃; for 12h; Inert atmosphere; stereoselective reaction; | 15 In the reaction flask was added 0.3 mmol of o-methyl phenylacetylene, 0.3 mmol p-methylphenyl cyanide, 0.3 mmol of potassium tert-butoxide, 0.3 mmol of tert-butyl alcohol, 1 ml of dimethyl sulfoxide, in after stirring at 80 ° C nitrogen protective stop heating and stirring 12 hours, cooled to room temperature.The reaction was washed with 15mL water, then extracted three times with ethyl acetate (each with I OmL), combined organic layers were dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and then purified by column chromatography to give the desired product, column chromatography eluent used was a volume ratio of 100: 1 n-hexane and ethyl acetate mixed solvent, 75% yield. |
75% | With potassium <i>tert</i>-butylate; <i>tert</i>-butyl alcohol In dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere; stereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In a 25 mL reactor,Sodium tert-butoxide (0.058 g, 0.6 mmol) and tetrakis (triphenylphosphine) palladium were added(0.017 g, 0.015 mmol) was added and the mixture was purged with nitrogen. After 5 mL of tetrahydrofuran was added, 4-methylphenylacetonitrile (0.079 g,0.6 mmol) and <strong>[86-52-2]1-chloromethylnaphthalene</strong> (0.053 g, 0.3 mmol) were added and stirred at 30 C for 12 h.The reaction solution was stirred in air for 10 h. Column chromatography (silica gel, 200-300 mesh; developing solvent, petroleum ether: ethyl acetate = 50: 1) to give 4-methyl- (4'-methylphenyl) -1-naphthylmethanone 0.064 g , Yield 82%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With copper(l) iodide; water; sodium hydroxide In methanol at 80℃; for 24h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium hexamethylsilazane In toluene; Petroleum ether at 100℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With C41H44ClIrN2O4; potassium hydroxide In toluene at 135℃; for 4h; | |
70% | With C24H22N6Ni; potassium <i>tert</i>-butylate In toluene at 95℃; for 30h; | |
68% | With C13H16MnN2O3S(1+)*Br(1-); potassium hydroxide In toluene at 140℃; for 36h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: (4-methylphenyl)acetonitrile With methylmagnesium bromide; lithium chloride In tetrahydrofuran; diethyl ether at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,2-dimethylmalononitrile In tetrahydrofuran; diethyl ether at 80℃; for 6h; Inert atmosphere; Stage #3: ethyl iodide In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere; | 4.2.3. General procedure A: synthesis of malononitriles fromprimary nitriles using MeMgBr General procedure: Step 1: To an 8-mL culture tube with stir bar was added lithium chloride (1.1 equiv) and the flask was flame-dried under vacuum and cooled under an atmosphere of N2. THF (1.0 M) was added, followed by the appropriate nitrile (1.0 equiv). While stirring, methylmagnesium bromide (1.1 equiv of a solution in Et2O) was added dropwise at r.t., and the solutionwas stirred at r.t. for 30 min under an atmosphere of N2. A 1.1M stock solution of dimethylmanononitrile (DMMN) or dibenzylmalononitrile (DBMN) inTHF was prepared and added at r.t. (1.1 equiv of a 1.1M solution inTHF, reaction volume 0.50M with respect to nitrile starting material). The reaction was stirred at 80 C for 6 h under an atmosphere of N2. Step 2: The reaction was cooled to r.t. and DMF was added to bring the reaction solvent to a 1:1 THF/DMF ratio (0.25Mof a 1:1 THF/DMF mixture with respect to nitrile starting material). The desired electrophile (1.2 equiv) was added in a single portion. Ifthe electrophile was a solid, it was added with the DMF as a 0.60Mstock solution. The reaction was stirred at 80 C for 16 h, or until complete conversion was achieved as judged by TLC. The reaction was cooled to r.t., opened to air, quenched with 1M aq. HCl, and extracted with EtOAc (3). The organic fractions were combined,dried over MgSO4, and concentrated. The crude residue was purified by flash column chromatography to yield the desired malononitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With lithium tert-butoxide In dimethyl sulfoxide at 80℃; for 12h; Inert atmosphere; | 6 Example 6 Under a nitrogen atmosphere, add 0.2 mmol of p-methylphenylacetonitrile to a 25-ml reaction bottle equipped with a reflux condenser,0.6 mmol lithium tert-butoxide, 0.6 mmol α-trifluoromethylstyrene, 4 ml dimethyl sulfoxide,The reaction system was stirred at 80°C for 12 hours,Stop heating and stirring, cool to room temperature, add water to quench the reaction, add ethyl acetate to extract the reaction solution,The ethyl acetate layer was subjected to rotary evaporation under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product,The column chromatography eluent used was a petroleum ether: ethyl acetate mixed solvent with a volume ratio of 30:1; the yield of the product was 92%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With 1,10-Phenanthroline; potassium <i>tert</i>-butylate In toluene at 120℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | Stage #1: (4-methylphenyl)acetonitrile; methyl iodide With sodium hydride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; Stage #2: With diisobutylaluminium hydride In toluene at -78℃; for 4h; Inert atmosphere; Stage #3: diethyl p-nitrobenzylphosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With C15H25Cl2N3NiO3; potassium <i>tert</i>-butylate In octane at 120℃; for 24h; Schlenk technique; Inert atmosphere; |
Tags: 2947-61-7 synthesis path| 2947-61-7 SDS| 2947-61-7 COA| 2947-61-7 purity| 2947-61-7 application| 2947-61-7 NMR| 2947-61-7 COA| 2947-61-7 structure
[ 19853-10-2 ]
2-([1,1'-Biphenyl]-2-yl)acetonitrile
Similarity: 0.92
[ 19853-10-2 ]
2-([1,1'-Biphenyl]-2-yl)acetonitrile
Similarity: 0.92
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