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CAS No. : | 3034-34-2 | MDL No. : | MFCD00017133 |
Formula : | C8H6N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FUKWTMJZHKZKFA-UHFFFAOYSA-N |
M.W : | 146.15 | Pubchem ID : | 76427 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 39.25 |
TPSA : | 66.88 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.85 cm/s |
Log Po/w (iLOGP) : | 1.0 |
Log Po/w (XLOGP3) : | 0.48 |
Log Po/w (WLOGP) : | 0.66 |
Log Po/w (MLOGP) : | 0.56 |
Log Po/w (SILICOS-IT) : | 0.95 |
Consensus Log Po/w : | 0.73 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.39 |
Solubility : | 6.01 mg/ml ; 0.0411 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.45 |
Solubility : | 5.14 mg/ml ; 0.0352 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.05 |
Solubility : | 1.3 mg/ml ; 0.00889 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.13 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P301+P310-P305+P351+P338 | UN#: | 3439 |
Hazard Statements: | H301-H315-H319-H335 | Packing Group: | Ⅲ |
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 |
---|---|---|
96% | Stage #1: terephthalonitrile With Br(1-)*C24H30N4Rh(1+); water In isopropyl alcohol at 25℃; for 0.5h; Inert atmosphere; Stage #2: With potassium <i>tert</i>-butylate In isopropyl alcohol at 25℃; for 12h; Inert atmosphere; | |
96% | With water In dimethyl sulfoxide at 100℃; Green chemistry; | |
94% | With sodium tetrahydroborate In ethanol; water at 80℃; for 4h; regioselective reaction; |
93% | With 4-(benzyloxy)-1-hydroxy-2,2,6,6-tetramethylpiperidine In dichloromethane at 50℃; for 2h; | |
92% | With tetra(n-butyl)ammonium hydroxide In ethanol; water at 80℃; for 6h; Green chemistry; chemoselective reaction; | |
91% | With sodium azide; water at 90℃; for 0.5h; | General procedure for amide synthesis General procedure: To an aqueous mixture of nitrile (1 mmol) in water (7 mL) was added NaN3 (0.1 mmol, 0.0065 g), then the reaction mixture was stirred vigorously in an oil bath preset at 90 °C for the appropriate time as mentioned in Table 1. After completion of the reaction (monitoredby TLC), the reaction mixture was cooled and the precipitated-outsolid was filtered and washed with water (3 × 5 mL) to give the pure product. The products were identified by their 1H NMR spectra and their physical data (m.p.) were compared with those described in the literature. Spectral data for the selected compound are as follows. |
85% | With copper(II) acetate monohydrate In water; acetic acid at 100℃; | |
85% | With water at 110℃; for 6h; | 2.2 General Procedure for Hydration of Nitriles to Amides General procedure: Two milli liter water at room temperature was added to astirred mixture of nitrile (1mmol) and catalyst (40mg) thenheated with an oil bath maintained at 110°C, and stirred. After completion of the reaction (monitored by TLC), thecatalyst was removed from the reaction mixture by externalmagnet. Then the mixture was extracted with ethyl acetate,subsequently purified by column chromatography on silicagel to provide the corresponding amide products. |
77% | With water at 130℃; for 0.5h; Microwave irradiation; | |
75% | With water at 130℃; for 0.75h; Microwave irradiation; | |
72% | With water at 100℃; for 0.75h; Microwave irradiation; | |
72% | With C34H38N6NiO2(2+)*2Cl(1-); water In isopropyl alcohol at 70℃; for 6h; Schlenk technique; Inert atmosphere; | |
15% | With water; palladium diacetate; acetic acid; scandium tris(trifluoromethanesulfonate) at 30℃; for 24h; | |
1% | With oxygen; triethylamine In acetonitrile for 17h; Irradiation; | |
With pyridine; ions-exchanger | ||
With C40H45ClN3O2PRu In methanol; water 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. | |
With nitrile hydratase from Rhodococcus rhodochrous J1 Y68T/W72Y mutant In aq. phosphate buffer at 35℃; for 4h; Enzymatic reaction; regioselective reaction; | ||
88 %Chromat. | With fac-[(CO)3Mn(iPr2P(CH2)2PiPr2)(triflato)]; water In tetrahydrofuran at 100℃; for 18h; Schlenk technique; Inert atmosphere; Glovebox; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium amide In dimethyl sulfoxide Sealed tube; | |
With hydrogenchloride; ethanol; benzene Behandeln des Reaktionsprodukts mit aethanol. Ammoniak; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium hydroxide | ||
With ammonium hydroxide In ethyl acetate for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium azide; ammonium chloride In N,N-dimethyl-formamide at 100 - 110℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With tetra-N-butylammonium tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 1h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With pyridine at 100℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sodium carbonate In methanol for 4.5h; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In tetrahydrofuran at -78 - 25℃; for 2h; 5 equiv. MeCeCl2; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium hydride In acetonitrile at 0 - 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With sodium hydride In N,N-dimethyl-formamide at 0℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With ammonium chloride; N-ethyl-N,N-diisopropylamine; 2-(1-oxypyridin-2-yl)-1,1,3,3-tetramethylisothiouronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 0.5h; | |
58% | With tris[2-phenylpyridinato-C2,N]iridium(III); dipotassium hydrogenphosphate; borane-ammonia complex; di-<i>tert</i>-butyl dicarbonate; magnesium chloride In acetonitrile at 20℃; for 36h; Schlenk technique; Irradiation; Green chemistry; | |
Multi-step reaction with 2 steps 1: (COCl)2, DMF / CH2Cl2 / Heating 2: conc. NH4OH / ethyl acetate / 0.17 h |
Multi-step reaction with 2 steps 1: 2 h / 80 °C / Ionic liquid 2: ammonium acetate; triethylamine / 3 h / 80 °C / Ionic liquid | ||
With ammonia at 250℃; for 0.5h; | A Amide Intermediate Preparation Example A General procedure: Into a 1L open reactor was added 500g of carboxylic acid raw material (chemically pure) and stirring was turned on (600 r/min) from the reactorThe bottom is continuously fed with ammonia gas (chemical purity, water content of 5.1% by weight, flow rate of 100 g/min) to the carboxylic acid feed. After the reaction was allowed to proceed for TC hours at the reaction temperature TA, ammonia gas flow was stopped. The contents of the reactor were sampled and subjected to nuclear magnetic proton and elemental analysis to characterize the amide intermediate. Specific reaction conditions and characterization results are shown in Table A-1, Table A-2, Table A-3, Table A-4, Table A-5 and Table A-6. These characterization results show that the amide intermediates obtained have an extremely high purity (above 99%).In this embodiment, the ammonia gas can be directly replaced with waste ammonia gas (from Yangzi Petrochemical Plant, containing approximately50wt% of ammonia gas, the rest were toluene, oxygen, nitrogen, steam, carbon monoxide, and carbon dioxide, and the flow rate of this waste ammonia was 130g/min). | |
Stage #1: 4-cyanobenzoic Acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.333333h; Inert atmosphere; Stage #2: With ammonium hydroxide In dichloromethane at 20℃; for 3h; Inert atmosphere; | ||
Multi-step reaction with 2 steps 1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 20 °C / Cooling with ice 2: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With thionyl chloride at 50 - 60℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With potassium carbonate In acetone at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | Stage #1: 4-cyanobenzamide With oxalyl dichloride In dichloromethane for 0.666667h; Heating; Stage #2: Quinoline N-oxide In dichloromethane for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | Stage #1: 4-cyanobenzamide With oxalyl dichloride In dichloromethane for 0.666667h; Heating; Stage #2: isoquinoline N-oxide In dichloromethane at 20℃; for 0.666667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 28 percent / NaH / dimethylformamide / 2 h / 0 °C 2: 96 percent / acetonitrile / 2 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NH4Cl, NaN3 / dimethylformamide / 18 h / 100 - 110 °C 2: Et3N / dimethylformamide / 3 h / 20 - 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: NH4Cl, NaN3 / dimethylformamide / 18 h / 100 - 110 °C 2: Et3N / dimethylformamide / 3 h / 20 - 25 °C 3: 37 percent / morpholine-iodine complex / benzene / 16 h / 20 - 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3% | With acetic acid for 20h; Heating / reflux; | 38 A stirred solution of ethyl 2-chloroacetoacetate (5.0 g, 30 mmole) in glacial AcOH (10 ml) was treated with 4-cyanobenzamide (J. Med. Chem. 1991, 34, 1630; 8.9 g, 61 mmole) and heated at reflux, under argon, for 20h. On cooling, the mixture was concentrated in vacuo, diluted with H2O (50 ml) and extracted with Et2O (2 x 150 ml). The combined organic extracts were washed with dilute aqueous K2CO3 solution, dried (MgSO4) and concentrated to dryness in vacuo. The residue was purified by silica gel chromatography, eluting with Et2O/petrol gradient, to afford the title compound as a yellow oil (0.26 g, 3%). MS: m/z (MH+) = 257. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | Stage #1: 4-cyanobenzamide With Lawessons reagent In tetrahydrofuran; 1,2-dimethoxyethane at 50℃; for 3h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; 1,2-dimethoxyethane at 20℃; for 0.333333h; Inert atmosphere; regioselective reaction; | |
39% | With Lawessons reagent In toluene for 2h; Heating / reflux; | 350.1 EXAMPLE 350; N-((2-(4-(N,N-Dimethylcarbamimidoyl)phenyl)thiazol-4-yl)methyl)-5-chlorothiophene-2- carboxamide (94); SCHEME 15; Step 1 :; [0903] Combined amide 81 (0.64 g, 4.1 mmol), Lawesson's reagent (1.00 g, 2.4 mmol) and 15 mL of toluene in a flask equipped with a condenser. The resulting beige suspension was refluxed for two hrs at which time all starting amide was consumed as determined by HPLC. The reaction was cooled, filtered through silica gel and concentrated, then purified by eluting through a short plug of silica gel (eluted with dichloromethane) affording the desired thioamide (88) as an orange solid (0.260 g, 39%). 1H NMR (OMSO-d6, 400 MHz): δ 10.12 (s, IH), δ 9.71 (s, IH), δ 7.90 (d, 2H), δ 7.84 (d, 2H). |
With Lawessons reagent In tetrahydrofuran at 23℃; for 1h; | 4.2. Preparation of thioamides 2. General procedure General procedure: Amides (1 mmol) and Lawesson's reagent (490 mg, 1.2 mmol) were added to dry THF (15 mL). The reaction mixture was stirred at room temperature for 1 h, or heated under reflux for 5 h in the case of the 4-nitro derivative. The solvent was evaporated under reduced pressure and the residue was partitioned between aq NaHCO3 (25 mL) and ethyl acetate (25 mL). The organic solvent was separated and dried over anhydrous MgSO4. The crude product was further purified by silica gel flash chromatography, using hexane-ethyl acetate (4:1), to yield the corresponding thioamides as yellow solids (42-60%). 4-Nitrothioamide (2ff),38 4-cyanothiobenzamide (2gg)39 and 3-cyanothiobenzamide (2hh),40 3-methoxythiobenzamide (2ii)41 have been previously reported. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In toluene;Heating / reflux; | EXAMPLE 338; N-((2-(4-(N,N-Dimethylcarbamimidoyl)phenyl)oxazol-4-yl)methyl)-5-chlorothiophene-2- carboxamide (87).; SCHEME 14; Step 1 :; [0887] Combined amide 81 (5.00 g, 31 mmol), dibromoacetone 82 (13 g, 62 mmol) and 60 mL of toluene in a flask equipped with a condenser. The mixture was refluxed overnight, then was checked by HPLC the following day which showed complete consumption of the starting material. The reaction was concentrated and purified by silica gel chromatography (dichloromethane as eluent) affording desired product 83 as a beige solid (5.21 g, 60%). 1H NMR (DMSO-J6, 400 MHz): delta 8.12 (d, 2H), delta 7.71 (m, 3H), delta 4.40 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | 30 Example 30 The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 4.83 g of p-cyanobenzoic acid (yield 96%, based on p-cyanobenzamide). The p-cyanobenzoic acid obtained had a purity of 97%. | |
95% | With sodium nitrite In sulfuric acid | 19 Example 19 Example 19 Sodium nitrite (2.07 g) was dissolved in a 70 wt. % aqueous sulfuric acid solution (100 ml), and p-cyanobenzamide (2.92 g) was added to the resultant solution. The mixture was allowed to react at room temperature for one hour with stirring. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 2.77 g of p-cyanobenzoic acid (yield 95%). High performance liquid chromatographic analysis revealed that the p-cyanobenzoic acid obtained had a purity of 99% or more. |
94% | 28 Example 28 The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 4.73 g of p-cyanobenzoic acid (yield 94%, based on p-cyanobenzamide). High performance liquid chromatographic analysis revealed that the p-cyanobenzoic acid obtained had a purity of 99% or more. |
92% | With acetic anhydride; acetic acid; sodium nitrite In water | 22 Example 22 Example 22 p-Cyanobenzamide (14.6 g), sodium nitrite (20.7 g), acetic acid (200 ml), and acetic anhydride (20 ml) were mixed and stirred vigorously at 5° C. To the mixture, trifuloroacetic acid (35 g) was added dropwise over three hours, and further stirred vigorously for five hours. The solvent was removed under reduced pressure, and water (300 ml) was added to the residue. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 13.4 g of p-cyanobenzoic acid (yield 92%). The p-cyanobenzoic acid obtained had a purity of 98%. |
86% | With sulfuric acid; acetic acid; sodium nitrite In water | 21 Example 21 Example 21 p-Cyanobenzamide (1.46 g) and acetic acid (20 ml) were mixed and stirred vigorously at room temperature. To the mixture, sodium nitrite (2.07 g), and immediately thereafter, 95 wt. % sulfuric acid (3 g) was added and stirred vigorously for one hour. The acetic acid was removed under reduced pressure, and water (40 ml) was added to the residue. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 1.26 g of p-cyanobenzoic acid (yield 86%). The p-cyanobenzoic acid obtained had a purity of 95%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide | 29 7-(4-Cyanobenzamido)-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno [3,2-b]pyran EXAMPLE 29 7-(4-Cyanobenzamido)-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno [3,2-b]pyran The title compound was prepared as described in Example 3 starting with 6-bromo-7-hydroxy-5-6-dihydro-5,5-dimethyl-7H-thieno [3,2-b]pyran (6.73 g, 25.6 mmol), sodium hydride (2.14 g, 53.8 mmol), 4-cyanobenzamide (12.0 g, 82.1 mmol) and N,N-dimethylformamide (75 ml) to give the product, after recrystallization from dichloromethane and hexanes, 0.82 g (10%) as a colorless solid; mp 177°-178° C.; 1R(KBr): 3420, 1648, 1545 and 1496 cm-1; MS: m/z 329 (MH+); 1 H NMR (CDCl3) δ 1.35 (s,3H),1.50 (s,3H), 3.79 (dd,J=7.8 Hz, J=2.5Hz, 1H, simplifies to d, J-7.8Hz with D2 O), 4.31 (d,J=2.5Hz, 1H, exchanges with D2 O), 5.17 (m, 1H), 6.56(bd, J=6.8Hz, 1H), 6.63(d,J=5.4 Hz,1H), 7.18(d,J=5.4 Hz, 1H), 7.78 (d,J=8.2 Hz, 2H) and 7.91 (d, J=8.2 Hz,2H). Anal. Calcd for C17 H16 N2 O3 S: C,62.18; H,4.91; N,8.53; S,9.75. Found: C,62.10; H, 4.74; N, 8.21; S,9.56. | |
In N,N-dimethyl-formamide | 29 7-(4-Cyanobenzamido)-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno [3,2-b]pyran EXAMPLE 29 7-(4-Cyanobenzamido)-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno [3,2-b]pyran The title compound was Prepared as described in Example 3 starting with 6-bromo-7-hydroxy-5-6-dihydro-5,5-dimethyl-7H-thieno[3,2-b]pyran (6.73 g, 25.6 mmol), sodium hydride (2.14 g, 53.8 mmol), 4-cyanobenzamide (12.0 g, 82.1 mmol) and N,N-dimethylformamide (75 ml) to give the product, after recrystallization from dichloromethane and hexanes, 0.82 g (10%) as a colorless solid; mp 177°-178° C.; 1R(KBr): 3420, 1648, 1545 and 1496 cm-1; MS: m/z 329 (MH+); 1 H NMR (CDCl3): δ 1.35(s,3H),1.50(s,3H),3.79 (dd,J=7.8 Hz, J=2.5 Hz, 1H, simplifies to d, J-7.8 Hz with D2 O), 4.31 (d,J=2.5 Hz, 1H, exchanges with D2 O), 5.17 (m, 1H), 6.56(bd, J=6.8 Hz, 1H), 6.63(d,J=5.4 Hz, 1H), 7.18(d,J=5.4 Hz, 1H), 7.78 (d,J=8.2 Hz, 2H) and 7.91 (d, J=8.2 Hz,2H). Anal. Calcd for C17 H16 N2 O3 S: C,62.18; H,4.91;N,8.53 S,9.75. Found: C,62.10; H, 4.74; N, 8.21; S,9.56. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium carbonate; In methanol; sulfuric acid; | EXAMPLE XII 4-Amidino-benzoic acid amide-hydrochloride Dry HCl gas is passed for 2 hours through a solution of 17.5 g of 4-cyano-benzoic acid amide in 700 ml of methanol cooled in an ice/water bath (washing bottle containing concentrated sulphuric acid provided in front). The solution is stirred at ambient temperature and the conversion is monitored by thin layer chromatography. After the reaction is complete the reaction solution is evaporated down at a bath temperature of 25 to 35 C. in a rotary evaporator, the residue is dissolved in 300 ml of methanol and the solution is mixed with 10.0 g of ammonium carbonate with thorough stirring. The mixture is stirred for 16 hours at ambient temperature, the precipitate is removed by suction filtering, washed with a little water and dried in vacuo. Yield: 8.5 g (35% of theory). By concentrating the filtrate and triturating the residue with a little water, suction filtering and drying, a further 8.8 g (37% of theory) of product can be obtained. Melting point: over 280 C., Rf value: 0.09 (silica gel; methylene chloride/methanol/conc. ammonia solution=2:1:0.25) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With formic acid; phosphorus pentachloride | XI.A A. A. 4-Cyano-N-[dichlorophosphinyl]benzamide A suspension of 18.1 g (0.12 mole) of 4-cyanobenzamide, 25.8 g (0.12 mole) of phosphorus pentachloride and 250 ml of AR carbon tetrachloride was stirred and heated at 70° until the HCl gas evolution had subsided; ca. 25 min. The solution was cooled to 30° and 5.9 g (0.12 mole) of 97% formic acid was added while maintaining a temperature of 30°. After stirring for 30 min., the product was collected, washed with AR carbon tetrachloride and dried to give 52 g, m.p. shrinks 162°-165°, darkens 218°, decomposes >300°. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | R.40 Reference Example 40 Reference Example 40 In substantially the same manner as in Reference Example 31, 4-cyanobenzamide was allowed to react with 1,3-dichloroacetone to give 4-chloromethyl-2-(4-cyanophenyl)oxazole. The yield was 41%. Recrystallization form ethyl acetate-hexane gave colorless prisms, mp 134-135° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With hydroxylamine In ethanol; water at 78℃; for 18h; | 27 Intermediate 27: 4-ramino(hvdroxyimino)methyllbenzamideTo a solution of 4-cyanobenzamide (512 mg; 3.93 mmol) in abs. EtOH (3 mL) was added hydroxylamine (0.8 mL; 12 mmol) (50% in water) and the mixture was heated to 78°C for 18 hours. The mixture was poured into a crystallizing dish and the solvent allowed to evaporate. The residue was washed with copious amounts of EtOAc, dry MeOH and dry MeCN which was filtered through a hydrophobic frit and the solvent removed in vacuo. Intermediate 27 was isolated as a yellow solid (513 mg; 79%). 1H NMR: (DMSO-d6, 400MHz) δ 9.81 (1 H, s), 8.01 (1 H, s), 7.89 (2H, d, J = 8.2 Hz), 7.77 (2H, d, J = 8.2 Hz), 7.40 (1 H, s), 5.91 (2H, s). |
With hydroxylamine In ethanol; water Heating / reflux; | A General Method A : amidoxime preparationA solution of hydroxy1amine (10 mmol) 50% in water was added to a solution of R-CN (10 mmol) in EtOH (10 ml) . The reaction mixture was heated at reflux overnight. The resulting mixture was concentrated and dry under vacuum to afford the different amidoximes (Table 3). Intermediates of the invention that were synthesized according to General Method A are listed in Table 3 below |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With 10% Pd/C; sodium fluoride; potassium iodide In PEG4000; water at 160℃; for 2h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With silver nitrate In ethanol; water byproducts: silver chloride; under N2 atm. mixt. Ru complex and AgNO3 in water/EtOH (1:1) was heated at reflux for 2 h, ppt. was filtered, ligand was added and heated at reflux for 4 h, react. mixt. was cooled, NH4PF6 was added; ppt. was collected by filtration, washed with water, EtOH, Et2O, dried in vac.; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: 4-cyanobenzamide With Lawessons reagent; boron trifluoride diethyl etherate In tetrahydrofuran; 1,2-dimethoxyethane at 20℃; for 3h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; 1,2-dimethoxyethane at 20℃; for 0.333333h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 4-cyanobenzamide With N-Bromosuccinimide; iron(II) chloride In acetonitrile at 20℃; for 0.0166667h; Stage #2: ethylthioacetic acid methyl ester In acetonitrile at 45℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With (1,3-(dicyclohexylphosphino)propane )Pd(ethylene); ammonia; potassium carbonate In dimethyl sulfoxide at 110℃; for 24h; Schlenk technique; Inert atmosphere; | |
32 %Chromat. | With ammonia; palladium diacetate; catacxium A In 1,4-dioxane at 130℃; for 20h; Autoclave; | |
30 %Chromat. | With 1,1'-bis-(diphenylphosphino)ferrocene; ammonia; palladium diacetate In 1,4-dioxane at 130℃; for 20h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With tris-(dibenzylideneacetone)dipalladium(0); (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; ammonium carbamate; sodium hydrogencarbonate In 1,4-dioxane at 100℃; for 20h; Inert atmosphere; | |
40% | With 2-(2'-pyridyl)(di(1-adamantyl)phosphino)benzene; ammonia; palladium diacetate In 1,4-dioxane at 120℃; for 16h; Autoclave; | |
53 %Chromat. | With ammonia; palladium diacetate; catacxium A In 1,4-dioxane at 80℃; for 30h; Autoclave; |
54 %Chromat. | With 1,1'-bis-(diphenylphosphino)ferrocene; ammonia; palladium diacetate In 1,4-dioxane at 100℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: (4-cyanophenyl)zinc(II) iodide; Trichloroacetyl isocyanate In tetrahydrofuran at -20 - 25℃; Inert atmosphere; Stage #2: With methanol; potassium carbonate In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 120℃; for 1.16667h; | 28 4-cyanobenzamide (327.0 mg, 2.237 mmol) and N,N-dimethylformamide diethyl acetal (0.53 ml, 3.09 mmol) were combined and heated to 120°C. A short path distillation apparatus was used to collect the ethanol that was liberated during the reaction. The reaction mixture was a dark purple solution that slowly turned lighter until it had become an amber solution. After 70 minutes, the reaction mixture solidified. The reaction mixture was cooled to room temperature and was placed under high vacuum overnight to give the title compound (432.7 mg, 2.150 mmol) as a yellow solid.1H NMR (CD3OD, 600 MHz, ppm) δ 3.24 (s, 3H, NMe), 3.26 (s, 3H, NMe), 7.78 (d, 2H, ArH), 8.32 (d, 2H, ArH), 8.65 (s, 1H).Mass Spectrum: (ΕSI) m/z = 202.09 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver carbonate In acetonitrile at 115℃; for 10h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 10% CuO-ZnO on activated carbon In toluene at 100℃; for 4h; Inert atmosphere; | 6. Typical procedure for the use of a heterogeneous catalyst General procedure: Calculated amount of catalyst (for example 60 mg), benzaldehyde oxime 4 (670 mg) and 1.1 mL toluene as a solvent were taken in an oven-dried, nitrogen purged Schlenk tube. Then the mixture was purged with nitrogen and stirred at 100 °C for 4 h. After set reaction time, the mixture was allowed to cool to room temperature, diluted with 2 mL ethanol, and filtered. The analysis of filtered reaction mixture was carried out by gas chromatography (Varian 3900) equipped with CP-Sil 5CB capillary column (15 m length and 0.25 mm diameter) and a flame ionization detector (FID). GC oven temperature was programmed from 60 to 110 °C at the rate of 8 °C/min and 111 to 300 °C at the rate of 25 °C/min. Helium was used as a carrier gas. Temperatures of injection port and FID were kept constant at 295 and 300 °C, respectively. Retention times of different compounds were determined by injecting pure compound under identical conditions. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 58% 2: 42% | With nickel(II) chloride dihydrate In acetonitrile at 80℃; Molecular sieve; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With iron(II) chloride tetrahydrate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide In tetrahydrofuran at 70℃; for 2h; | |
86% | With diethyl chlorophosphate at 120℃; for 0.25h; Neat (no solvent); | |
82% | Stage #1: 4-cyanobenzamide With N-methylbenzamide; phenylsilane; C28H18ClMnN2O2; potassium <i>tert</i>-butylate In tetrahydrofuran at 50℃; Inert atmosphere; Glovebox; Sealed tube; Stage #2: With sodium hydroxide In tetrahydrofuran for 2h; Inert atmosphere; Glovebox; Sealed tube; Stage #3: Glovebox; Inert atmosphere; |
72% | at 315℃; for 1h; | A Nitrile Product Preparation Example A General 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 99%).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. |
With N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; zinc trifluoromethanesulfonate In tetrahydrofuran at 70℃; for 24h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With Cu(II) on nano silica functionalized triazine dendrimer In water at 20℃; for 0.5h; Green chemistry; | |
96% | With Cu(II)-metformin immobilized ongraphene oxide In water at 100℃; for 0.5h; Green chemistry; | |
80% | With [Ru(κ(3)-tpy)(κ(1)-P-PPh2Py)Cl2] In toluene for 12h; Reflux; | 2.4. Catalytic activity General procedure: Mixture of the oxime (2.0 mmol) and the catalyst [Ru(κ3-tpy)(κ1-P-PPh2Py)Cl2)] (3) (13.3 mg, 0.02 mmol) was refluxed in toluene (1 mL) for appropriate time (refPreviewPlaceHolderTable 1). After completion of the reaction CH2Cl2 was added to reaction mixture and resulting solution was filtered through celite. The crude product was purified by column chromatography (silica gel, MeOH/CH2Cl2). After work-up amides were obtained in good yield (Table 1). |
80% | With Cu(II) complex on SiO2-coated Fe3O4 nanoparticles at 80℃; for 1h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Stage #1: 4-cyanobenzaldehyde With hydroxylamine hydrochloride; sodium hydrogencarbonate In water Stage #2: In water at 100℃; for 10h; | |
96% | With hydroxylamine hydrochloride; sodium carbonate In water at 80℃; for 48h; | |
95% | With hydroxylamine hydrochloride; sodium carbonate In water at 80℃; for 22h; Green chemistry; |
94% | With hydroxylamine hydrochloride; potassium carbonate In water at 80℃; for 20h; Schlenk technique; | 2.5. General procedure for the synthesis of amide bond General procedure: The mixture of benzaldehyde (1 mmol), NH2OHHCl (1.2 mmol),K2CO3 (1.1 mmol), DI-H2O (2 mL) were added to 10 mol % ofCuONRs/g-C3N4-NS catalyst in a Schlenk tube. Then, the reactionmixture was stirred at 80 C for 20 h. After completing the reaction,the catalyst was separated by centrifugation and organic phasepurified by column chromatography on silica to obtain the amideproduct 3. Finally, all primary amides were identified by 1H and13C NMR spectroscopy |
78% | With hydroxylamine hydrochloride; caesium carbonate In tetrahydrofuran; water at 0 - 250℃; for 0.0833333h; | |
77% | With hydroxylamine hydrochloride; caesium carbonate In acetonitrile at 60 - 65℃; | General experimental procedure for the synthesis of substituted benzamide derivatives: General procedure: To a stirred solution of acetonitrile (10 mL), aldehyde (1.0 mmol) and bioglycerol-based carbon catalyst (10 wt %) were added and stirred for 10 min. To this NH2OH·HCl (1.0 mmol) followed by Cs2CO3 (1.0 mmol) were added, after which the reaction mixture was heated at 60-65 °C until completion of the reaction as indicated by TLC. The reaction mixture was cooled to room temperature and catalyst was filtered, the solvent was removed by rotary evaporator. The crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography using ethyl acetate and hexane (2:8) as eluents to give the corresponding substituted benzamide derivative in (71-78%) yield. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra. |
76% | With tert.-butylhydroperoxide; sodium carbonate; ammonium chloride In acetonitrile at 50℃; for 0.666667h; Inert atmosphere; Green chemistry; | |
69% | With hydroxylamine; copper diacetate In water at 110℃; for 48h; | 4.2. General procedure for the synthesis of amides General procedure: To a solution of copper(II) acetate (0.04 mmol) in water (1 mL) were added the corresponding aldehyde (3, 2 mmol) and the hydroxylamine (4, 2 mmol). After 2 days stirring at 110 °C the mixture was quenched with a saturated solution of ammonium chloride (10 mL), or added ether (2 mL) for the recycling process. The mixture was extracted with AcOEt (3×10 mL) and washed with brine (10 mL), after drying with anhydrous MgSO4, the organic layer was filtered on Celite and the solvents were removed under low pressure (15-18 Torr). The product was purified recrystallization from chloroform/hexane mixtures to give the corresponding product 2. Amides 2a,262b,272c, 272d,172e,282f,292g,272h,172j,302k,172l30 and 2m17 are commercially available and were characterized by comparison of their physical and spectroscopic data with those of pure examples. Yields are included in Table 4 (Fig. 1 for recycling processes). Physical and spectroscopic data, as well as literature data for known compounds, follow. |
68% | With hydroxylamine In water at 110℃; for 12h; | 2.4. General procedure for the synthesis of amides from aldehydes General procedure: Aldehyde (1 mmol), hydroxylamine (1 mmol), polymer supported-Cu (II) catalyst (30 mg-10 mg) and solvent (2 m/L) were added in a 10 mL round bottom flask and the reaction mixture was stirred at 110 °C. The progress of the reaction was by TLC. The crude product obtained was purified by column chromatography with ethyl acetate:hexane as 1:5 eluent system. |
68% | With hydroxylamine In water at 110℃; for 12h; | 2.4. General procedure for the synthesis of amides from aldehydes General procedure: Aldehyde (1 mmol), hydroxyl amine (1 mmol), polymer supported-Cu (II) catalyst (30 mg-10 mg) and solvent (2 m/L) were added in a 10 mL round bottom flask and the reaction mixture was stirred at110 °C. The progress of the reaction was by TLC. The crude product obtained was purified by column chromatography with ethyl acetate:hexane as 1:5 eluent system. |
52% | With copper(I) oxide; potassium carbonate; ammonium chloride In water; acetonitrile at 80℃; for 4h; Inert atmosphere; | |
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; zinc(II) oxide / 80 °C 2: Cu(II) complex on SiO2-coated Fe3O4 nanoparticles / 1 h / 80 °C / Green chemistry | ||
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; zinc(II) oxide / 80 °C 2: Cu(II)–metformin immobilized ongraphene oxide / water / 0.5 h / 100 °C / Green chemistry |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.2% | With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; silver trifluoroacetate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In N,N-dimethyl-formamide; at 8℃; for 9h; | In room temperature,To a suitable amount of an organic solvent (polyethylene glycol 200 in a volume ratio of 1: 2 and DMF (N, N-dimethylformamideAmine), 100 mmol of the compound of the above formula (I) was added,180 mmol of the compound of the above formula (II)18 mmol of catalyst [1,1'-bis (diphenylphosphino) ferrocene] nickel dichloride,Iodobenzoic acid (IBX) and 22 mmol of trifluoroacetic acid as the oxidizing agent, and then the temperature was raised to 8 C and the reaction was stirred at the same temperature for 9 hours; After completion of the reaction, a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, sufficiently shaken with ethyl acetate extraction 2-3 times, the combined organic phase, anhydrous magnesium sulfate drying, vacuum concentration,The residue was subjected to silica gel column chromatography through 300-400 mesh to give the compound of the above formula (III)The yield was 96.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 8 h / Inert atmosphere; Reflux 2: hydrazine hydrate; acetic acid / 1 h / Reflux 3: caesium carbonate; copper(l) iodide; 8-quinolinol / N,N-dimethyl-formamide; water / 0.5 h / 150 °C / Microwave irradiation | ||
Multi-step reaction with 2 steps 1.1: 8 h / Reflux; Inert atmosphere 1.2: 1 h / Reflux 2.1: caesium carbonate; 8-quinolinol / copper(l) iodide / N,N-dimethyl-formamide; water / 0.5 h / 150 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: 4-cyanobenzamide; <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal for 8h; Reflux; Inert atmosphere; Stage #2: With hydrazine hydrate; acetic acid for 1h; Reflux; | 15.1 Step 1. 4-(lH-[l,2,4]Triazol-3-yl)-benzonitrile. The general procedure outlined by Lin et. al. (J. Org. Chem. 1979, 44, 4163) for preparation of 3-(4-nitrophenyl)-lH- [l,2,4]triazole was used. 4-Cyanobenzamide (21.63 g, 0.148 mol) was dissolved in DMF- DMA (100 rnL) and was stirred at reflux under N2 for 8 h. The mixture was concentrated to dryness and suspended in AcOH (50 rnL). The vessel was then charged with hydrazine monohydrate (7.18 mL, 0.148 mmol) and stirred at reflux for 1 h before concentration. The desired 4-(lH-[l,2,4]triazol-3-yl)-benzonitrile was obtained in 98% purity by trituration with Et2O followed by filtration (12.17 g, 0.072 mol, 48%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 27h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-Bromosuccinimide / tetrachloromethane / 4 h / 20 °C / Irradiation 2: ammonium hydroxide; iodine / 18 h / 20 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With C42H58NO3PPdS(2-); potassium acetate; tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With tris-(dibenzylideneacetone)dipalladium(0); tris(2-morpholinophenyl)phosphine; potassium carbonate In water; <i>tert</i>-butyl alcohol at 85℃; for 10h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With sodium azide; iodine; sodium hydrogencarbonate In water at 100℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With ammonia; hydrogen In toluene at 120℃; for 16h; Autoclave; | |
98 %Chromat. | With formic acid; palladium 10% on activated carbon; triethylamine In tetrahydrofuran at 40℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | Stage #1: Cyclohexyl iodide; 4-cyanobenzamide With copper(l) iodide; lithium tert-butoxide In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 65% 2: 18% | With water; palladium diacetate; acetic acid; scandium tris(trifluoromethanesulfonate) at 30℃; for 24h; | |
With chitosan-supported ruthenium catalyst (ChRu) In water at 120℃; for 1h; Microwave irradiation; Sealed tube; Overall yield = 7 %; | ||
With nitrile hydratase from Rhodococcus rhodochrous J1 W72Y mutant In aq. phosphate buffer at 35℃; for 4h; Enzymatic reaction; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 78% 2: 20% | Stage #1: 4-cyanobenzaldehyde With ammonia at -33℃; for 1h; Inert atmosphere; Stage #2: With potassium permanganate at -33℃; for 1h; Inert atmosphere; Reflux; Stage #3: With sodium sulfite | General Procedure for the Oxidation of Aldehydes to Amidesin Liquid Ammonia General procedure: Under an argon atmosphere, liquid NH3 (25 mL) was condensedin a two-neck round-bottom flask immersed in a dry ice coolingbath and equipped with a dry ice reflux condenser. Aldehyde(7.34 mmol) was added, and the resulting solution (or suspension)was stirred for 1 h. KMnO4 (7.34 mmol, 1.16 g) was added,the cooling bath was removed, and the reaction mixture wasstirred for another hour with gentle reflux of NH3. Na2SO3 (22.0mmol, 2.78 g) was added, the reflux condenser was removed,and the NH3 was allowed to evaporate spontaneously. The darkbrownresidue was treated with 6 M HCl (30 mL), and theresulting precipitate was filtered, washed with H2O (100 mL)and sat. aq NaHCO3 (20 mL). All products were recrystallizedfrom EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 4-cyanobenzaldehyde With ammonia at -33℃; for 1h; Inert atmosphere; Stage #2: With potassium permanganate for 1h; Inert atmosphere; Reflux; | General Procedure for the Oxidation of Aldehydes to Amidesin Liquid Ammonia General procedure: Under an argon atmosphere, liquid NH3 (25 mL) was condensedin a two-neck round-bottom flask immersed in a dry ice coolingbath and equipped with a dry ice reflux condenser. Aldehyde (7.34 mmol) was added, and the resulting solution (or suspension)was stirred for 1 h. KMnO4 (7.34 mmol, 1.16 g) was added,the cooling bath was removed, and the reaction mixture wasstirred for another hour with gentle reflux of NH3. Na2SO3 (22.0mmol, 2.78 g) was added, the reflux condenser was removed,and the NH3 was allowed to evaporate spontaneously. The darkbrownresidue was treated with 6 M HCl (30 mL), and theresulting precipitate was filtered, washed with H2O (100 mL)and sat. aq NaHCO3 (20 mL). All products were recrystallizedfrom EtOH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With water; sodium hydroxide In ethanol at 90℃; for 17h; | |
78% | With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 20℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With copper (II) trifluoroacetate hydrate; palladium diacetate In dimethyl sulfoxide at 130℃; for 10h; Sealed tube; Inert atmosphere; | 14 General procedure for the synthesis of aryl nitriles 1b-28b General procedure: Aryl iodide (0.7 mmol, 1 equiv), tert-butyl isocyanide (2.1 mmol, 237 μL, 3 equiv), Pd(OAc)2 (0.035 mmol, 8 mg, 5 mol %), Cu(TFA)2*xH2O (1.4 mmol, 405 mg, 2 equiv) and DMSO (2.5 mL) were added to a 15 mL sealed tube, and stirred at 130 °C for 4-12 h under nitrogen. After completion of the reaction indicated by TLC, the mixture was extracted with Et2O (510 mL). The combined organic phases was dried over Na2SO4, and concentrated under vacuum. Then the residue was purified by column chromatography on silica gel using petroleum ether (30-60 °C)/Et2O as eluant to provide the pure target product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon; ammonium carbamate; potassium iodide In acetonitrile at 90℃; for 8h; Autoclave; Green chemistry; | |
72% | With 1H-imidazole; ammonium carbamate; triethylamine In N,N-dimethyl-formamide at 130℃; for 12h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: 4-cyanobenzamide; Hexafluoroacetone With pyridine In benzene at 20℃; for 0.5h; Stage #2: With thionyl chloride In benzene at 20℃; for 2h; | 1 4.3. General procedure for preparation of imines 2b-d General procedure: To mixture of 0.1 mol of benzamide in 50 ml of benzene, 0.2 mol of pyridine, 0.11 mol of hexafluoroacetone was bubbled at stirring at 20°C during 30 min. Then, 0.1 mol of SOCl2 was added, and the mixture was stirred during 2 h. The formed precipitate was filtered off. After the solvent removal, the residue was fractionated for 2b,d or crystallized from hexane for 2c. 4.3.1. 4-Cyano-N-(1,1,1,3,3,3-hexafluoropropan-2-ylidene)benzamide 2b. Yield 82%; bp 81-82 °C (1 Torr). 1H NMR (200 MHz, CDCl3, δ): 7.86 (d, 2H, CHAr, 3JHH = 8.0 Hz), 8.05 (d, 2H, CHAr, 3JHH = 8.0 Hz). 19F NMR (188.29 MHz, CDCl3, δ): -68.3 s. Calc. for C11H4F6N2O: C, 44.91, H, 1.37, N, 9.52. Found: C, 44.76, H, 1.26, N, 9.44. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With potassium phosphate; t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate at 110℃; for 16h; Inert atmosphere; | 155A tert-butyl 4-{10-[(4-cyanobenzoyl)amino]-2-oxo-l,2-dihydropyrimido[l,2-b]indazol-4- yl}piperidine-l -carboxylate Under argon, tert-butyl 4-(10-bromo-2-oxo-l,2-dihydropyrimido[l,2-b]indazol-4-yl)piperidine-l- carboxylate (200 mg, 447 μιηο), 4-cyanobenzamide (163 mg, 1.12 mmol), Tripotassium phosphate (133 mg, 626 μιηο), tBuBrettPhos (13.0 mg, 26.8 μιηο), and tBuBrettPhos Pd G3 (22.9 mg, 26.8 μιηο1)νεΓε dissolved in l-Methoxy-2-propanol (5.0 ml, 52 mmol). The mixture was stirred at 110 °C for 16 h and then purified via reverse phase chromatography (Method: Reprosil C18; 10 μιη; 125x30 mm / flow: 50 ml/min / solvents: A = water (0,01% formic acid), B = Acetonitrile / gradient 0.00-4.25 min = 20%B, 4.50min = 30%B, 19.00-22.50min = 100%B, 22.75-25.00min = 20%B) which afforded the product after drying in vacuo. The obtained amout was 98 mg (100 % purity, 43 % of theory). LC-MS (Method 1): Rt = 1.17 min; MS (ESIpos): m/z = 513 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With dmap In dichloromethane at 0 - 20℃; Inert atmosphere; | |
85% | With dmap In acetonitrile at 20℃; for 15h; Inert atmosphere; Sealed tube; | |
84.5% | With dmap In dichloromethane at 0 - 23℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6h; Schlenk technique; Inert atmosphere; Sealed tube; | |
80% | With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6h; Inert atmosphere; Sealed tube; | 31 Example 1 Compound (1a) General procedure: Under argon protection, NiCl2·6H2O (0.05mmo 1,11.9mg), dppf (0.06mmol, 33.3mg), Zn (0·2mmol, 13.0mg), DMAP (1.0mmol, 122.2mg), Zn(CN)2 (0.8mmol) , 93.9mg), p-Chloroanisole (1.0 mmol, 140.6 mg) and acetonitrile (5.0 mL) were sequentially added in a 25.0 mL sealed tube, then directly put it into the oil bath at 60 °C, and heating was stopped after 6h, and cooled to room temperature, the reaction solution was directly filtered through a short silica gel column, washed with dichloromethane, concentrated and purified by silica gel column chromatography( given that the product is most easily pulled out, in order to avoid loss of sample mix, unless otherwise noted, both are wet method). Eluent: petroleum ether / ethyl acetate = 20:1, the product was 117.2 mg as a white solid, yield 88%, and 1H NMR purity was greater than 98%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 6h; Schlenk technique; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | With palladium diacetate; ammonium bicarbonate; dicyclohexyl-carbodiimide; triphenylphosphine In acetonitrile at 100℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | With hydroxylamine hydrochloride; sodium hydrogencarbonate In methanol at 75℃; for 6h; | 4 4.2.1.2. General procedure for the synthesis of 8a-e General procedure: To a round-bottom flask equipped with a stir bar was added 7a-e (1.0 eq), hydroxylamine hydrochloride (2.0 eq), NaHCO3 (4.0 eq), and methanol (5.0mL/mmol). The reaction was refluxed and stirred in a pre-heated 75°C oil-bath for 6h. The reaction mixture was cooled to room temperature, and the precipitate was filtered off and washed with methanol. The filtrate was concentrated in vacuo without further purification |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: 4-formylbenzamide With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: With potassium hydrogen difluoride; 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate In water at 20℃; for 3h; | |
82% | With ammonium hydroxide; oxygen In acetonitrile at 90℃; for 24h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With [2,2]bipyridinyl; aluminum (III) chloride; nickel(II) acetylacetonate; zinc(II) oxide In 1,2-dimethoxyethane at 145℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate In 1,2-dichloro-ethane for 8h; Inert atmosphere; Reflux; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: 4-cyanobenzamide With [(aNHC)KN(SiMe3)2]2; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 40℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: With water; sodium hydroxide In diethyl ether; toluene at 40℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique; Stage #3: With hydrogenchloride In diethyl ether; water Inert atmosphere; Glovebox; Schlenk technique; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With copper(I) oxide; ammonia In dimethyl sulfoxide at 130℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With ammonium carbonate In dimethyl sulfoxide at 25℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With [bis(acetoxy)iodo]benzene; ammonium carbamate In 2,2,2-trifluoroethanol at 0 - 20℃; for 23.5h; Inert atmosphere; | N-Substituted Ureas; General procedure B General procedure: (Diacetoxyiodo)benzene (1.0 mmol, 2.0 equiv) was added in one portion to a stirred solution of the amide (0.5 mmol, 1.0 equiv) and ammonium carbamate (AC) (0.75 mmol, 1.5 equiv) in trifluoroethanol (1.25 mL) at 0 °C under argon. After 30 min at 0 °C, the reaction mixture was allowed to reach room temperature and was left to stir for 9 h. Additional amounts of PIDA and AC (1.0 equiv each) were added at rt and the reaction mixture was stirred for 12 h at rt. After concentration of the reaction mixture under reduced pressure, the crude product was purified by flash chromatography on silica gel. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With triethylamine In dichloromethane at 20℃; for 1h; Cooling with ice; | 1 Example 1: Preparation of compound II-1: In a 100 ml reaction round bottom flask, first add 3 mmol of compound I, dissolve it in 30 ml of dichloromethane solution, add 6 mmol of oxalyl chloride under an ice bath, and finally add 3 drops of N,N-dimethylformamide. Stir at room temperature for 2 hours; after the reaction is complete, concentrate under reduced pressure to remove excess oxalyl chloride and solvent to obtain p-cyanobenzoyl chloride for use; add 3 mmol of methylamine compound to another 100 ml reaction round bottom flask , 30 ml of dichloromethane was dissolved, and 3 millimoles of triethylamine and p-cyanobenzoyl chloride were sequentially added under an ice bath, stirred at room temperature for 1 hour, and the reaction was detected by dot plate and concentrated under reduced pressure to obtain p-cyanobenzamide Compound; This compound was dissolved in 30 ml of ethanol, and 3.6 mmoles of compound hydroxylamine hydrochloride and N,N-diisopropylethylamine were added in turn, and stirred at room temperature for 3 hours. After the reaction was completed, it was concentrated under reduced pressure and acetic acid Dilute with ethyl ester, wash with water, extract 3 times with ethyl acetate, combine the organic layers, wash with saturated sodium chloride, dry with anhydrous sodium sulfate, filter with suction, remove the solvent under reduced pressure, and purify the residue by 100-200 mesh silica gel column chromatography The eluent is petroleum ether: ethyl acetate at 60-90 degrees Celsius. According to the characteristics of the reactants, the volume ratio is 5:1 to 1:10 to obtain solid compound II-1, 76%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 3h; Cooling with ice; | 1 Example 1: Preparation of compound II-1: In a 100 ml reaction round bottom flask, first add 3 mmol of compound I, dissolve it in 30 ml of dichloromethane solution, add 6 mmol of oxalyl chloride under an ice bath, and finally add 3 drops of N,N-dimethylformamide. Stir at room temperature for 2 hours; after the reaction is complete, concentrate under reduced pressure to remove excess oxalyl chloride and solvent to obtain p-cyanobenzoyl chloride for use; add 3 mmol of methylamine compound to another 100 ml reaction round bottom flask , 30 ml of dichloromethane was dissolved, and 3 millimoles of triethylamine and p-cyanobenzoyl chloride were sequentially added under an ice bath, stirred at room temperature for 1 hour, and the reaction was detected by dot plate and concentrated under reduced pressure to obtain p-cyanobenzamide Compound; This compound was dissolved in 30 ml of ethanol, and 3.6 mmoles of compound hydroxylamine hydrochloride and N,N-diisopropylethylamine were added in turn, and stirred at room temperature for 3 hours. After the reaction was completed, it was concentrated under reduced pressure and acetic acid Dilute with ethyl ester, wash with water, extract 3 times with ethyl acetate, combine the organic layers, wash with saturated sodium chloride, dry with anhydrous sodium sulfate, filter with suction, remove the solvent under reduced pressure, and purify the residue by 100-200 mesh silica gel column chromatography The eluent is petroleum ether: ethyl acetate at 60-90 degrees Celsius. According to the characteristics of the reactants, the volume ratio is 5:1 to 1:10 to obtain solid compound II-1, 76%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 3.5. General Procedure for the Preparation of Compounds (2), (5-25) General procedure: To a solution of the appropriate carboxamide compound (1.06 mmol, 1.5 equiv.) in dry DMF (3mL) at 0 °C under N2, 60% sodium hydride in oil (25.5 mg, 1.06 mmol, 1.5 equiv) were added portionwise. The resulting mixture were added dropwise to a solution of 4-chloro-2-(trichloromethyl)quinazoline (4) (200 mg, 0.71 mmol, 1.0 equiv.) in dry DMF (2 mL) at 0 °C under N2.The reaction was stirred overnight at rt. Then, the excess of NaH was hydrolyzed with ice. Thereaction mixture was extracted with EtOAc and washed three times with brine. The organic layerwas dried with Na2SO4, filtered, and evaporated. The crude product was purified by silica gel columnchromatography and recrystallized from appropriate solvent to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; | 36 Example 1: Preparation of benzonitrile: General procedure: After synthesizing the Ru complex according to the method shown in A, add the Ru complex, alkali, primary amine and organic solvent to the reaction tube according to the mol ratio of 1:100:200:1000.The reaction system was stirred for 24 hours at 100°C.Gas chromatography monitors the complete disappearance of the raw materials and stops the reaction.Centrifuge, take the supernatant and add 5ml of water, extract with dichloromethane (5ml×3), combine the organic phases, dry over anhydrous magnesium sulfate, filter, evaporate the filtrate under reduced pressure to remove the organic solvent, and purify by column chromatography to obtain Colorless liquid, the yield is 95.4%. |
87 %Chromat. | With C68H64Cl2N6P2Ru2(4+)*2F6P(1-)*2Cl(1-); caesium carbonate; N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With C24H20ClN2OPRu; potassium <i>tert</i>-butylate; hydrogen In tetrahydrofuran at 110℃; for 36h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With bis(acetylacetonate)nickel(II); copper(l) iodide; dimethylaminoacetic acid; caesium carbonate In N,N-dimethyl acetamide at 120℃; for 16h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With hydroxylamine hydrochloride; 2,4,6-triphenylpyrylium tetrafluoroborate; oxygen; ammonium bromide In acetonitrile at 40℃; for 24h; Molecular sieve; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With lithium hydroxide monohydrate In water at 20℃; for 2h; | |
40% | With allyl bromide In methanol at 60℃; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With trifluoroacetic acid sodium salt; [(PAd2-DalPhos)Ni(4-CNPh)Cl]; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 110℃; for 18h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With ammonium bicarbonate; copper(II) nitrate In dimethyl sulfoxide at 140℃; for 40h; Autoclave; | Representative Procedure for Conversion of Various Arylethenesto Aromatic Nitriles General procedure: To a stainless steel autoclave lined with Teflon, 0.5 mmol substrate,0.075 mmol Cu(NO3)2, 1 mmol (NH4)2CO3, and 2 mLDMSO were added. Then the reactor was filled with 2 MPaoxygen and was heated under magnetic stirring at 140 °C for 30h or 40 h (Caution: the use of the high-pressure oxygen ispotentially hazardous. Thus, experiments using the high-pressureoxygen must only be carried out under rigorous safety precautions,and it is required to use the appropriate high-pressurereactor to avoid the potential leakage or explosion of the gas).Once the reaction time was reached, the mixture was cooled toroom temperature, diluted with 30 mL diethyl ether, and filteredvia a Celite pad. The organic mixture was washed withwater (3 × 5 mL), dried with anhydrous sodium sulfate, and concentratedin vacuum. GC analysis provided the GC yields of theproduct with an internal standard. In addition, the combinedcrude product from another 1-5 parallel experiments was purifiedby column chromatography and identified by 1H NMR and13C NMR spectroscopy. All the products are the known compounds,and the analytical data of several typical compoundsare as follows: |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With ammonium hydroxide; oxygen In neat (no solvent) at 120℃; for 6h; Sealed tube; | General Procedure for preparation of amides catalyzed by Fe3O4*SiO2-SMTU-Cu General procedure: A sealed pressure vessel was charged with phenylacetic acids (68.0 mg, 0.5 mmol), Fe3O4*SiO2-SMTU-Cu catalyst (20 mg), and aqueous ammonia solution (28 wt% in H2O; 1.5 mL). The resulting solution was stirred at 120 °C under O2 (monitored by TLC and GC) for 6 hours. Upon completion of the reaction, the catalyst was separated using magnetic stirring bar and ethyl acetate (20 mL) was added, the organic layer was washed with saturate NaHCO3 (20 mL) solution twice, brine (20 mL) once, the combined aqueous layers was extracted with EtOAc (20 mL) twice. The combine organic layers were dried over anhydrous Na2SO4. The solvents were removed via rotary evaporator and the residue was purified with flash chromatography (silica gel, ethyl acetate: petroleum ether=2:1) to give amide products. |
Tags: 3034-34-2 synthesis path| 3034-34-2 SDS| 3034-34-2 COA| 3034-34-2 purity| 3034-34-2 application| 3034-34-2 NMR| 3034-34-2 COA| 3034-34-2 structure
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H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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