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CAS No. :2208-59-5 MDL No. :MFCD00453948
Formula : C12H9N3 Boiling Point : -
Linear Structure Formula :- InChI Key :UYWWLYCGNNCLKE-UHFFFAOYSA-N
M.W : 195.22 Pubchem ID :247634
Synonyms :

Safety of [ 2208-59-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2208-59-5 ]

* 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.

  • Downstream synthetic route of [ 2208-59-5 ]

[ 2208-59-5 ] Synthesis Path-Downstream   1~52

  • 1
  • [ 872-85-5 ]
  • [ 95-54-5 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
99% With air In methanol at 20℃; Irradiation; Green chemistry;
98% With ammonium cerium (IV) nitrate; dihydrogen peroxide at 50℃; for 1h;
98% With isocyanurate bridging periodic mesoporous organosilica In ethanol for 1.08333h; Reflux;
96% With oxygen In methanol for 2h; 2-4 General procedure: Weigh compound 1 (o-phenylenediamine compound, 0.2 mmol) and compound 2 (aldehyde compound, 0.2 mmol) and dissolve them in 2 mL of methanol and 10 mg of CbzCMP-10, add them to a 10 mL reaction flask, and continuously feed oxygen Under the conditions of , the visible light intensity was 20W/cm -2 blue LED light for 2 hours continuously, and then the solvent was spin-dried and separated by chromatography to obtain the corresponding product. The structural formula and yield of the product benzimidazole compounds are shown in Table 1.
94% With benzotrithiophene and triphenylamine-based covalent organic framework In ethanol at 20℃; Irradiation;
92% With oxygen; pyrographite In xylene at 110 - 115℃; for 1h;
92% With AlPO4 supported ethylenediamine-chromium(III)-salen complex nanoparticles; air In ethanol at 20℃; for 5h; Green chemistry; General procedure for the synthesisof 2-arylbenzimidazoles in the presenceof chromium(III) salen complex nanoparticlessupported on AlPO4 General procedure: A mixture of o-phenylenediamine (1.0 mmol), aryl aldehyde(1.0 mmol) and chromium(III) salen complex nanoparticles supported on AlPO4(2.0 mol%) in ethanol (5 mL) was stirred at room temperature. After completion of the reaction (TLC), the mixture was centrifuged and rinsed with ethanol (3 × 15 mL). The recovered nanocatalyst was dried and stored for another consecutive runs. The solvent was evaporated to give the crude product, which was purified by silica gel column chromatography employing n-hexane/ethyl acetate (8:1) as eluent.
92% Stage #1: pyridine-4-carbaldehyde; 1,2-diamino-benzene With anhydrous sodium carbonate In ethanol at 20℃; for 0.0833333h; Stage #2: pyridine-4-carbaldehyde In ethanol at 50℃; for 2h; 2 4.2. Synthesis of 2-(pyridin-4-yl)-1H-benzo[d]imidazole (3a) A mixture of o-phenylenediamine (1a, 1 mmol), Fe3O4NCs-OPO3H (0.05 g) and absolute ethanol (2 mL) was put into a 25 mLround-bottom flask and stirred for 5 min at room temperature. Then, asolution of pyridin-4-carbalehyde (2, 1 mmol) in ethanol (2 mL) wasadded dropwise to this mixture at 50 °C under vigorous stirring for 2 h.After completion of reaction (monitored by TLC, n-hexane/EtOAc70:30), the catalyst was isolated from reaction mixture by externalmagnet. Then, water and sodium carbonate were added to the reactionmixture and the separated solid was collected as pure product 3a. Yield92%; yellowish solid; mp 216-218 °C; IR (KBr, cm-1) νmax: 1610 (C]N). 1H NMR (DMSO-d6, 500 MHz) δ: 13.28 (s, 1H, NH), 8.76 (d, 2H,J=5.5 Hz, Ha pyridine), 8.09 (d, 2H, J=5.5 Hz, Hb pyridine), 7.73 (d,1H, J=7.8 Hz, H4 benzimidazole), 7.59 (d, 1H, J=7.8 Hz, H7 benzimidazole),7.30 (t, 1H, J=7.8 Hz, H5 benzimidazole), 7.24 (t, 1H,J=7.8 Hz, H6 benzimidazole). 13C NMR (DMSO-d6, 125 MHz) δ: 150.5,148.8, 137.1, 124.5, 122.6, 120.3, 111.8. Anal. Calcd for C12H9N3(195.22): C, 73.83; H, 4.65; N, 21.52. Found: C, 73.72; H, 4.43; N,21.74.
90% In methanol at 20℃; for 3h;
90% With sodium metabisulfate In N,N-dimethyl-formamide for 3h; Reflux; 3.1 General Procedure for the Synthesis of Compounds 1-27 General procedure: Equimolar mixture of pyridine carboxaldehyde deriva-tives (1 mmol) and sodium metabisulphite (1 mmol) in DMF (10 mL) was stirred for 10 to 15 min, followed by the addi-tion of o-phenylene diamine/2-aminothiophenol (1 mmol) into it and refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was poured into crushed ice, precipitates were formed which were collected by filtration to afford compounds 1-27 in good yields. Recrystallization from methanol yielded pure crystals.
89% With sodium hydrogen sulphite In lithium hydroxide monohydrate at 100℃; for 0.333333h; Green chemistry; chemoselective reaction; General procedure for the synthesis of 2-substitutedbenzimidazole General procedure: In a round-bottomed flask (10 mL) equipped with a magnetic stirrer, a mixture of aldehyde (1.0 mmol) and NaHSO3(11.0 eq, 1.14 g) in H2O (4.0 mL) was prepared. When the mixture reached refluxing temperature, o-phenylenediamine derivatives (1.0 mmol) were added. The resulting mixture was stirred for appropriate time and monitored by HPLC (Hypersil GOLD 250 × 4.6 mm, 5 μm). After completion of the reaction, the reaction mixture was vacuum filtered after cooling to room temperature by a glass funnel. The residues were washed by water (4 mL × 2), dried in air dry oven and characterized by physical and spectral properties.
87% With 2,6-dimethyl-1-nitropyridin-1-ium trinitromethanide In neat (no solvent) at 20℃; for 0.416667h; Green chemistry;
82% With tris(pentafluorophenyl)borate In ethanol at 20℃; for 0.666667h; diastereoselective reaction; Typical experimental procedure for the synthesis of benzimidazole derivatives General procedure: A mixture of benzaldehyde 1 (1 mmol), o-phenylenediamine 5a (1 mmol) in EtOH (10 mL) was stirred magnetically at room temperature in the presence of B(C6F5)3 [5 mol %]. After completion of reaction, as indicated by TLC analysis, the solid obtained was filtered, washed with ethanol, dried and re-crystallize from ethanol to give pure product (6a). The assigned structures of the products were established from their spectral and physical properties and also by comparison with available literature data.
80% In methanol for 0.5h;
79% Stage #1: pyridine-4-carbaldehyde; 1,2-diamino-benzene In butan-1-ol at 100℃; for 1h; Green chemistry; Stage #2: With 1-butyl-3-methylimidazolium tungstate In butan-1-ol at 100℃; for 6h; Green chemistry; 2.5 General procedure for synthesis of 2-arylbenzimidazoles 6 General procedure: The mixture of o-phenylenediamines 4b (0.6mmol, 1.2 equiv), aldehydes 2 (0.5mmol, 1 equiv) in 5mL 1-butanol was stirred at 100°C with oil bath for 1h. [BMIm]2[WO4] (0.1mmol, 53mg, 0.2 equiv) was added to reaction mixture for further 6h at 100°C in the open air. The following procedures are similar to the synthesis of 2-arylbenzothiazoles 5. The pure products were obtained by silica gel column chromatography.
78% Stage #1: pyridine-4-carbaldehyde; 1,2-diamino-benzene In ethanol at 20℃; for 2h; Stage #2: With [bis(acetoxy)iodo]benzene In ethanol at 20℃; for 1h; Further stages.;
78% Stage #1: pyridine-4-carbaldehyde; 1,2-diamino-benzene In ethanol at 20℃; for 2h; Stage #2: With [bis(acetoxy)iodo]benzene In ethanol at 20℃; for 1h;
75% With sodium meta-bisulphite for 0.0138889h; microwave irradiation;
60% Stage #1: pyridine-4-carbaldehyde; 1,2-diamino-benzene In acetonitrile at 25℃; for 0.0833333h; Stage #2: With Novoprime base 268 In acetonitrile at 25℃; for 2h; chemoselective reaction;
49% In methanol at 60℃; for 1h;
48% With disodium metabisulfite Microwave irradiation;
With air; mesoporous silica; palladium(0); benzene
With nitrobenzene
In N,N-dimethyl-formamide at 110℃;
With 1-hydroxy-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one In dimethyl sulfoxide at 25℃; for 16h; General procedure for the one-pot conversion of alcohols to benzimidazoles: In a typical experiment, the primary alcohol (0.5-0.6 mmol) and IBX (1.1 equiv) were stirred in DMSO at ca. 20 °C. Once the oxidation of alcohol to aldehyde was complete, as judged from TLC analysis, o-phenylenediamine (1.1 equiv) was introduced into the reaction mixture and the reaction mixture was allowed to stir at room temperature until the aldehyde disappeared. At the end of the reaction, DMSO was removed under high vacuum, and the residue was treated with 1.0 M NaHCO3 solution until the pH was 8-9. The organic matter was extracted with ethyl acetate. Regular work-up followed by silica-gel column chromatography led to pure benzimidazoles, which were characterized spectroscopically.
With air In methanol at 20℃; Irradiation; Inert atmosphere;
With sodium hydrogen sulphite In lithium hydroxide monohydrate Reflux;
99 %Spectr. With activated (H3O)[Cd(II)(4-(3,5-dicarboxylphenyl)picolinate)] metal-organic framework In [D3]acetonitrile at 20℃; for 3h;

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[3]Dekamin, Mohammad G.; Arefi, Elham; Yaghoubi, Amene [RSC Advances, 2016, vol. 6, # 90, p. 86982 - 86988]
[4]Current Patent Assignee: HUNAN INST ENGINEERING - CN114591248, 2022, A Location in patent: Paragraph 0068-0073; 0076-0080
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[14]Location in patent: experimental part Kundus, Nabanita; Audhya, Anandalok; Abtab, Sk Md Towsif; Ghosh, Sanjib; Tiekink, Edward R. T.; Chaudhury, Muktimoy [Crystal Growth and Design, 2010, vol. 10, # 3, p. 1269 - 1282]
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  • 2
  • [ 55-22-1 ]
  • [ 95-54-5 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
96% With PPA at 210 - 270℃; for 0.05h; microwave irradiation;
88% Stage #1: pyridine-4-carboxylic acid; 1,2-diamino-benzene at 174.84℃; for 4 - 5h; Stage #2: With ammonium hydroxide In water
85% With Amberlyst-15 In water at 90℃; for 2.66667h; Irradiation; General procedure for the preparation of compound 3-5 General procedure: To a solution of o-phenylenediamine 1a, o-amino phenol 1b or o-amino thiophenol 1c (1.0 mmol) and aromatic acid (2, 1.2 mmol) in water (5 mL) was added Amberlyst-15 (10%, w/w) and the mixture was irradiated with ultrasound (40 KHz) continuously at 90 °C till the completion of the reaction(monitored by TLC) as indicated in Table 3. The solid separated was filtered, washed with diethyl ether (2 x 5 mL), dried and treated with EtOAc (15 mL). After stirring for 10 min the mixture was filtered to remove the insoluble catalyst. The filtrate was collected and concentrated under vacuum. The solid obtained was purified by recrystallization (column chromatography infew cases) to afford the desired products 3, 4 or 5.
85.9% With polyphosporic acid Microwave irradiation; 2.3. Synthesis of 2-(pyridin-4-yl)-(1H)-benzoimidazole (4PBI) Isonicotinic acid (1.477 g, 0.011 mol) and 1,2-phenylene diamine(1.081 g, 0.010 mol) were mixed and grinded. To the reactionsmixture, polyphosphoric acid (10 ml) was added.Subsequently, the reaction mixture was heated periodically underthe irradiation of microwave. After the completed reaction, twoblocks of ice were added to the mixture. When the reaction mixturewas cooled to room temperature, pure water (30 ml) waspoured to the mixture solution. The pH value of the solution wasadjusted to 7 by adding the NaOH solution (10%). Finally, the solidproduct was collected and further crystallized from pure water togive a needle-like crystal. Yield (85.9%, 1.675 g). M.p. 226-228 °C.The microanalyses of compound 4PBI are in good accordance withthat reported previously [23].
85.9% With polyphosphoric acid Microwave irradiation; 2.2. Synthesis of 2-Pyridin-4-yl-1H-benzoimidazole (4-PyBim) To a mixture solid of isonicotinic acid (1.477 g, 0.012 mol) and 12-phenylene diamine(1.081 mg, 0.010 mol), which were ground and mixed adequately, polyphosphoric acid(10 ml) was added. The reaction mixture was intermittently heated under microwave irradiationwith 100-watt power. Subsequently, two blocks of ice were added. The reactionmixture was allowed to cool to room temperature and then poured over water (30 ml). The pH of the reaction mixture was adjusted to 7 by adding 10% NaOH solution. The solidformed was ltered under reduced pressure and dried. Yield (85.9%, 1.675 g). m.p. 224-230 °C. The microanalysis of 4-PyBim was in accord with those of the compound reportedpreviously [22].
83% With PPA at 170 - 180℃; for 4h;
80% With PPA; Polyphosphoric acid (PPA) at 170 - 180℃; for 4h;
62% at 200℃; for 2.5h;
62% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In ethyl acetate at 160℃; for 0.5h; Microwave irradiation; Sealed tube; 2.3 Synthesis of benzimidazoles General procedure: A mixture of o-phenylenediamine (1 mmol), carboxylic acid (1 mmol), N,N-diisopropylethylamine (1.5 mmol) and propylphosphonic anhydride (1 mmol, 50% w/w in AcOEt) was irradiated for 30 min under microwave at 160 °C in a sealed tube. It was diluted with H2O, followed by alkalinization with saturated aqueous NaHCO3 solution. The precipitate was collected by filtration and washed thoroughly with H2O to afford the respective benzimidazole. If necessary, simple recrystallization was carried out in EtOH/H2O.
53% With polyphosphoric acid In ethylene glycol at 80 - 200℃;
42% Stage #1: pyridine-4-carboxylic acid; 1,2-diamino-benzene at 200℃; for 4h; Inert atmosphere; Stage #2: With sodium hydroxide In water Cooling with ice; Inert atmosphere;
40% With triphenyl phosphite In pyridine at 220℃; for 0.166667h; microwave irradiation;
at 250℃;
With hydrogenchloride at 150℃;
In dimethyl sulfoxide at 200℃; Yield given;
With polyphosphoric acid at 180℃; Inert atmosphere;
With polyphosphoric acid at 240℃; for 6h;
With polyphosphoric acid for 3h; Reflux;
Multi-step reaction with 2 steps 1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C 2: acetic acid / 120 °C
With boric acid In o-xylene at 140℃; for 16h;

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  • 3
  • [ 109-65-9 ]
  • [ 2208-59-5 ]
  • [ 134079-73-5 ]
YieldReaction ConditionsOperation in experiment
88% In N,N-dimethyl-formamide at 85 - 95℃; for 12h;
  • 6
  • [ 2208-59-5 ]
  • [ 148533-73-7 ]
YieldReaction ConditionsOperation in experiment
97.5% With sulfuric acid; nitric acid at 0 - 20℃; for 2h;
84% With sulfuric acid; nitric acid 1.) from 0 to 80 deg C, 1 h, 2.) RT, 4 h;
  • 7
  • [ 2208-59-5 ]
  • [ 100-39-0 ]
  • [ 51784-48-6 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide Heating;
With potassium iodide In acetonitrile Reflux; 1 General procedure for the preparation of compounds 4a-q General procedure: In a 25 mL round bottom flask, a mixture of compounds 3a, 3b or 3c(1 mmol), benzyl halide derivative (1.2 mmol) and a catalytic amountof KI in dry acetonitrile (5 mL) was refluxed for 1-4 h. After completionof the reaction (as monitored by TLC, n-hexane/EtOAc 50:50), the reactionmixture was cooled and the solvent was removed under reducedpressure. Afterward, the residue was triturated with diethyl ether (5 mL) to obtain the pure products 4a-q.
  • 8
  • [ 95-54-5 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 1,2-diamino-benzene With diethylaluminium chloride In toluene at 0 - 20℃; Stage #2: hydroxymethyl JandaJelTM resin-bound 4-pyridyl ester In toluene for 24h; Heating; Further stages.;
  • 9
  • [ 14254-57-0 ]
  • [ 95-54-5 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
93% With boron trifluoride diethyl etherate In 1,4-dioxane Heating;
  • 10
  • [ 2208-59-5 ]
  • [ 74-88-4 ]
  • [ 64262-98-2 ]
YieldReaction ConditionsOperation in experiment
77% With potassium hydroxide In acetone at 20℃; for 2h;
  • 11
  • [ 2208-59-5 ]
  • [ 1724-67-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97.5 percent / conc. nitric acid; conc. sulfuric acid / 2 h / 0 - 20 °C 2: 71.4 percent / Zn; aq. CaCl2 / ethanol / 2 h / Heating
  • 12
  • [ 615-42-9 ]
  • [ 33278-46-5 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
32% With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In 1-methyl-pyrrolidin-2-one at 170℃; Inert atmosphere;
  • 13
  • [ 2208-59-5 ]
  • [ 100-21-0 ]
  • 0.5C8H6O4*C12H9N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With manganese (II) acetate tetrahydrate In water at 160℃; for 120h;
  • 14
  • [ 2208-59-5 ]
  • [ 606-80-4 ]
  • [ 5970-45-6 ]
  • [ 1310-73-2 ]
  • [Zn2(dpa)(PyBIm)(H2O)(OH)]*1.5H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% In water hydrothermal react.; soln. of Zn(OAc)2*2H2O, H2dpa, PyHBIm and NaOH (1:1:1:2 mol) heated to 160°C for 96 h in Teflon-lined stainless steel reactor; slow cooling to room temp.; TGA; elem. anal.;
  • 15
  • [ 2208-59-5 ]
  • [ 109-64-8 ]
  • [ 1329069-20-6 ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: 2-(pyridin-4-yl)-1H-benzo[d]imidazole With sodium hydroxide In dimethyl sulfoxide at 60℃; for 0.5h; Stage #2: 1,3-dibromo-propane In dimethyl sulfoxide at 60℃; for 12h;
  • 16
  • [ 110-52-1 ]
  • [ 2208-59-5 ]
  • [ 1309581-69-8 ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 2-(pyridin-4-yl)-1H-benzo[d]imidazole With sodium hydroxide In dimethyl sulfoxide at 60℃; for 1h; Stage #2: 1,4-dibromo-butane In dimethyl sulfoxide at 60℃; for 12h;
  • 17
  • [ 2208-59-5 ]
  • [ 879-18-5 ]
  • [ 1449509-57-2 ]
YieldReaction ConditionsOperation in experiment
65% With sodium hydride In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;
  • 18
  • [ 2208-59-5 ]
  • [ 2243-83-6 ]
  • [ 1449509-68-5 ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydride In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;
  • 19
  • [ 2208-59-5 ]
  • [ 3163-27-7 ]
  • [ 1171591-76-6 ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydride In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;
  • 20
  • [ 2208-59-5 ]
  • [ 939-26-4 ]
  • [ 1449509-87-8 ]
YieldReaction ConditionsOperation in experiment
94% With sodium hydride In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;
  • 21
  • [ 100377-32-0 ]
  • [ 95-54-5 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
75% With boron trifluoride diethyl etherate In 1,4-dioxane at 100℃; for 1h; Inert atmosphere; General Procedure for the Synthesis of 2-substituted Benzoimidazoles 3a-l General procedure: To a solution of o-diaminobenzene (5.0 mmol, 0.5405 g) and Weinreb amide (N-methoxy-Nmethylbenzamide, 5.0 mmol, 0.82595 g) in dioxane (10 mL), boron trifluoride diethyl etherate (5.0 mmol) was added at room temperature. The reaction mixture was stirred for the specified time (Table 3) at 100 °C. TLC revealed the complete consumption of starting material. Subsequently hydrolysis was achieved by the addition of saturated NH4Cl solution (50 mL). The aqueous layer was extracted with ethyl acetate (3 X 25 mL), washed with water (2 X 25 mL), brine solution (2 X 25 mL), dried over anhydrous Na2SO4 and concentrated under vacuum to get crude product. This was purified by column chromatography over silica gel using hexane/ethyl acetate mixture in 1:1 ratios as eluent.
  • 22
  • [ 2208-59-5 ]
  • [ 1081112-34-6 ]
  • [ 1081112-10-8 ]
YieldReaction ConditionsOperation in experiment
92 mg With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 5h; Synthesis of 2-[2-(Pyridin-3-yl)ethyl]-1-{3-[4-(3-acetamidophenyl)piperidin-1-yl]propyl}-1H-benzimidazole (3o) General procedure: To a stirred solution of 40 mg (0.18 mmol) of 2-[2-(pyridin-3-yl)ethyl]-1H-benzimidazole (2o) in N,N-dimethylformamide (5 mL) were added 71 mg (0.22 mmol) of 3-[4-(3-acetamidophenyl)piperidin-1-yl]propyl methanesulfonate (6) and 75 mg (0.54 mmol) of K2CO3. The reaction mixture was stirred at 80 °C for 5 h. After cooling, water (50 mL) was added, and the mixture was extracted with ethylacetate (50 mL × 2). The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (5% MeOH/CH2Cl2) to obtain the title compound (75 mg, 87%).
  • 23
  • [ 114797-95-4 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
92% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In N,N-dimethyl-formamide at 110℃; for 5h;
  • 24
  • [ 54751-01-8 ]
  • [ 95-54-5 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
79% With pyridine N-oxide at 110℃; for 2h; General procedure for the synthesis of 2-substituted benzimidazoles General procedure: Primary alkyl bromide derivative (5 mmol), pyridine-N-oxide (12.5 mmol) and orthophenylenediamine derivative (5 mmol) are well mixed in a 25 mL round bottomed flask and placed in an oil bath on a magnetic stirrer hot plate at required temperature. The mixture was heated to selected temperature for required time (Table 2). After completion of the reaction (TLC, AcOEt-petroleum ether), the organic mixture was washed with dilute NaOH and filtered off. The filtrate was collected for recovery of pyridine. The resulting residue was recrystallized from EtOH-H2O to give the desired benzimidazole products. Pyridine was recovered from the filtrate (99.5%) by azeotropic distillation (bp. 92.6°C) and separation on sodium hydroxide. Resulting pyridine was oxidized with peracetic acid to the pyridine-N-oxide [46] which was then reused in reaction. All of the products are known compounds [47-57] and their identity was easily confirmed by comparison with authentic samples (mp, 1H-NMR, 13C-NMR).
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 20 °C 2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / N,N-dimethyl-formamide / 5 h / 110 °C
  • 25
  • [ 3731-53-1 ]
  • [ 95-54-5 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
65% With oxygen; iron(II) bromide In chlorobenzene at 110℃; for 18h; Schlenk technique; Green chemistry;
  • 26
  • [ 2208-59-5 ]
  • [ 121-91-5 ]
  • [ 7732-18-5 ]
  • cobalt(II) acetate [ No CAS ]
  • 2C12H9N3*C8H4O4(2-)*H2O*Co(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
52.4% With sodium hydroxide at 160℃; for 72h; Autoclave; High pressure; 2 2.2. Synthesis of [Co(IPA)(4PBI)]*H2O (1) A reaction mixture of 4PBI (0.0195 g, 0.1 mmol), cobalt acetate (0.0177 g, 0.1 mmol), isophthalic acid (IPA) (0.0166 g, 0.1 mmol) and water (6 ml) was stirred for 30 min and then transferred to a 15 ml Teflon-lined reactor. Subsequently the mixture was adjusted to pH 7 by adding NaOH (0.008 g, 0.2 mmol). After 3 days under an autogenous pressure at 160 °C, the reaction mixture was then cooled to room temperature at a rate of 5 °C h-1. Red acicular crystals suitable for single crystal X-ray diffraction were obtained (yield: 52.4% based on cobalt acetate). IR (KBr, cm-1): 3362 (w), 3061 (w), 1614 (s), 1543 (s), 1477 (m), 1429 (m), 1393 (s), 1314 (m), 1277 (w), 1221 (m), 1161 (w), 1109 (w), 1076 (w), 1016 (w), 962 (w), 837 (m), 743 (s), 719 (w), 698 (w), 563 (w), 519 (w), 434 (w).
  • 27
  • [ 2208-59-5 ]
  • [ 121-91-5 ]
  • [ 7732-18-5 ]
  • [ 543-90-8 ]
  • 2C12H9N3*C8H4O4(2-)*H2O*Cd(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
12.6% With sodium hydroxide at 160℃; for 72h; Autoclave; High pressure; 3 2.2. Synthesis of [Co(IPA)(4PBI)]*H2O (1) General procedure: A reaction mixture of 4PBI (0.0195 g, 0.1 mmol), cobalt acetate (0.0177 g, 0.1 mmol), isophthalic acid (IPA) (0.0166 g, 0.1 mmol) and water (6 ml) was stirred for 30 min and then transferred to a 15 ml Teflon-lined reactor. Subsequently the mixture was adjusted to pH 7 by adding NaOH (0.008 g, 0.2 mmol). After 3 days under an autogenous pressure at 160 °C, the reaction mixture was then cooled to room temperature at a rate of 5 °C h-1.
  • 28
  • [ 2208-59-5 ]
  • [ 100-21-0 ]
  • [ 7732-18-5 ]
  • [ 543-90-8 ]
  • 2C12H9N3*C8H4O4(2-)*Cd(2+)*H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
45.3% With sodium hydroxide at 160℃; for 72h; Autoclave; High pressure; 4 2.2. Synthesis of [Co(IPA)(4PBI)]*H2O (1) General procedure: A reaction mixture of 4PBI (0.0195 g, 0.1 mmol), cobalt acetate (0.0177 g, 0.1 mmol), isophthalic acid (IPA) (0.0166 g, 0.1 mmol) and water (6 ml) was stirred for 30 min and then transferred to a 15 ml Teflon-lined reactor. Subsequently the mixture was adjusted to pH 7 by adding NaOH (0.008 g, 0.2 mmol). After 3 days under an autogenous pressure at 160 °C, the reaction mixture was then cooled to room temperature at a rate of 5 °C h-1.
  • 29
  • nickel(II) nitrate hexahydrate [ No CAS ]
  • [ 2208-59-5 ]
  • [ 68432-95-1 ]
  • [ 7732-18-5 ]
  • C12H9N3*Ni(2+)*C10H8O4(2-)*H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
58.18% With sodium hydroxide at 160℃; for 72h; Autoclave; High pressure; 2.4. Synthesis of [Ni(L)(4PBI)(H2O)]n (1) A mixture of Ni(NO3)2*6H2O (0.0290 g, 0.1 mmol), 4PBI(0.0195 g, 0.1 mmol), NaOH (0.0072 g, 0.18 mmol), H2L (0.0194 g,0.1 mmol) and water (6 ml) were heated at 160° C for 3 days in a15 ml Teflon-lined vessel container. The reaction mixture wascooled to room temperature at a rate of 5 °C h-1. Green block crystalsof complex 1 suitable for X-ray diffraction analysis wereobtained (0.027 g, Yield: 58.18%) based on Ni (NO3)2. Elementalanalysis calcd (%) for C22H19NiN3O5 (464.10): C, 56.94; H, 4.13; N,9.05; found: C, 56.81; H, 4.11; N, 9.01. IR (KBr, cm-1): 3067(w),2970 (w), 1616(m), 1597(m), 1564(s), 1531(s), 1447(s), 1406(s),1317(m), 1282(m), 1238(w), 1126(w), 1061(w), 1022(m), 972(m),916(m), 866(m), 847(w), 818(m), 788(w), 761(m), 743(s), 694(m), 640(w), 563(w), 516(w), 438(w).
  • 30
  • cobalt(II) sulphate heptahydrate [ No CAS ]
  • [ 2208-59-5 ]
  • [ 68432-95-1 ]
  • [ 7732-18-5 ]
  • C12H9N3*C10H8O4(2-)*H2O*Co(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
58.14% With sodium hydroxide at 160℃; for 72h; Autoclave; High pressure; 2.4. Synthesis of [Ni(L)(4PBI)(H2O)]n (1) General procedure: A mixture of Ni(NO3)2*6H2O (0.0290 g, 0.1 mmol), 4PBI(0.0195 g, 0.1 mmol), NaOH (0.0072 g, 0.18 mmol), H2L (0.0194 g,0.1 mmol) and water (6 ml) were heated at 160° C for 3 days in a15 ml Teflon-lined vessel container. The reaction mixture wascooled to room temperature at a rate of 5 °C h-1. Green block crystalsof complex 1 suitable for X-ray diffraction analysis wereobtained (0.027 g, Yield: 58.18%) based on Ni (NO3)2.
  • 31
  • copper(ll) sulfate pentahydrate [ No CAS ]
  • [ 2208-59-5 ]
  • [ 68432-95-1 ]
  • [ 7732-18-5 ]
  • C12H9N3*C10H8O4(2-)*H2O*Cu(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
53.31% With sodium hydroxide at 120℃; for 72h; Autoclave; High pressure; 2.4. Synthesis of [Ni(L)(4PBI)(H2O)]n (1) General procedure: A mixture of Ni(NO3)2*6H2O (0.0290 g, 0.1 mmol), 4PBI(0.0195 g, 0.1 mmol), NaOH (0.0072 g, 0.18 mmol), H2L (0.0194 g,0.1 mmol) and water (6 ml) were heated at 160° C for 3 days in a15 ml Teflon-lined vessel container. The reaction mixture wascooled to room temperature at a rate of 5 °C h-1. Green block crystalsof complex 1 suitable for X-ray diffraction analysis wereobtained (0.027 g, Yield: 58.18%) based on Ni (NO3)2.
  • 32
  • [ 2208-59-5 ]
  • [ 68432-95-1 ]
  • cadmium sulfate hydrate [ No CAS ]
  • C12H9N3*C10H8O4(2-)*Cd(2+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.03% With sodium hydroxide In water at 160℃; for 72h; Autoclave; High pressure; 2.4. Synthesis of [Ni(L)(4PBI)(H2O)]n (1) General procedure: A mixture of Ni(NO3)2*6H2O (0.0290 g, 0.1 mmol), 4PBI(0.0195 g, 0.1 mmol), NaOH (0.0072 g, 0.18 mmol), H2L (0.0194 g,0.1 mmol) and water (6 ml) were heated at 160° C for 3 days in a15 ml Teflon-lined vessel container. The reaction mixture wascooled to room temperature at a rate of 5 °C h-1. Green block crystalsof complex 1 suitable for X-ray diffraction analysis wereobtained (0.027 g, Yield: 58.18%) based on Ni (NO3)2.
  • 33
  • [ 872-85-5 ]
  • [ 4403-69-4 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
90% With [bis(acetoxy)iodo]benzene; iodine In dichloromethane at 20℃; for 1h; chemoselective reaction;
  • 34
  • [ 2208-59-5 ]
  • cadmium(II) bromide tetrahydrate [ No CAS ]
  • [ 7732-18-5 ]
  • CdBr<SUB>2</SUB>(2-pyridin-4-yl-1H-benzoimidazole)<SUB>2</SUB>(H<SUB>2</SUB>O)<SUB>2</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
44.3% at 160℃; for 72h; High pressure; 2.6. Synthesis of [CdCl2(4-PyBim)2(H2O)2] (3) General procedure: A reaction mixture of CdCl2*5/2H2O (45.6 mg, 0.2 mmol), 4-PyBim (19.5 mg, 0.1 mmol), and water (10 ml) was added to a 15 ml Teflon reactor under autogenous pressure at 160 °C for3 days and then cooled to room temperature at 5 °C h-1. Pale yellow crystals of 3 were collected. (23 mg, Yield: 18.9%).
  • 35
  • [ 2208-59-5 ]
  • [ 7732-18-5 ]
  • cadmium(II) iodide [ No CAS ]
  • CdI<SUB>2</SUB>(2-pyridin-4-yl-1H-benzoimidazole)<SUB>2</SUB>(H<SUB>2</SUB>O)<SUB>2</SUB> [ No CAS ]
YieldReaction ConditionsOperation in experiment
22.7% at 160℃; for 72h; High pressure; 2.6. Synthesis of [CdCl2(4-PyBim)2(H2O)2] (3) General procedure: A reaction mixture of CdCl2*5/2H2O (45.6 mg, 0.2 mmol), 4-PyBim (19.5 mg, 0.1 mmol), and water (10 ml) was added to a 15 ml Teflon reactor under autogenous pressure at 160 °C for3 days and then cooled to room temperature at 5 °C h-1. Pale yellow crystals of 3 were collected. (23 mg, Yield: 18.9%).
  • 36
  • [ 26377-17-3 ]
  • [ 95-54-5 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
94% With ethanolamine-phosphoric acid functionalized polyacrylonitrile fibers (PANEAPF) In water at 80℃; for 8h; Green chemistry;
  • 37
  • zinc(II) nitrate hexahydrate [ No CAS ]
  • [ 2208-59-5 ]
  • [1,1′-biphenyl]-2,3,3′,5′-tetracarboxylic acid [ No CAS ]
  • [ 7732-18-5 ]
  • C16H6O8(4-)*2Zn(2+)*H2O*C12H9N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With sodium hydroxide at 160℃; for 120h; Autoclave; High pressure; 2.2.1. Synthesis of [Zn(H2btca)2(bpt)].H2O}n (1) General procedure: Zn(NO3)2.6H2O (0.1785 g, 0.6 mmol), H4btca (0.099 g,0.3 mmol), bpt (0.1339 g, 0.6 mmol), bpt = 1H-3,5-bis(4-pyridyl)-1,2,4-triazole, NaOH (4 drops, 1 mol/L aqueous solution) and H2O(12 ml) were mixed. Then the final mixture was sealed in a 23 mlTeflon-lined stainless vessel and heated at 160 °C for 120 h underthe autogenous pressure. The reaction system was then cooledwith a rate of 5 °C/min. The resulting yellow block-like crystalswere collected after washing with distilled water and dried inair. Yield: 61% (based on Zn).
  • 38
  • [ 872-85-5 ]
  • [ 28144-70-9 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
89% With tert.-butylhydroperoxide; iodine In water; acetonitrile at 20℃; for 2h; General Procedure for the Synthesis of Benzimadazoles (3a, 3j-3z) from 2-aminobenzamides and aldehydes General procedure: To an oven dried rb flask with a magnetic stir bar were added 2-amiobenzamide 1a (136.0 mg, 1.0 mmol), aldehyde derivative (1 mmol), iodine (52 mg, 0.2 mmol), and the mixture was stirred in 3 mL acetonitrile for 30 min at room temperature. Then aq. TBHP (70% solution in water, 0.26 mL, 2.0 mmol) was added and the mixture stirred at rt for about 1.5 h. After completion of the reaction (TLC monitoring), the reaction mixture was quenched by aq. Na2S2O3 solution (5%, 20 mL), extracted with ethyl acetate (10 mL × 3), and the combined organic layer was dried over anhydrous sodium sulphate. Removal of the solvent under reduced pressure left a crude mass which was purified by column chromatography using silica gel (25% EtOAc/hexane) to afford 3a (167 mg; 86% yield).
  • 39
  • [ 500-22-1 ]
  • [ 95-54-5 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
93% With MIL-101(Fe)-NH2 hexagonal microspindle catalyst In ethanol at 25℃; for 1h;
  • 40
  • [ 2208-59-5 ]
  • [ 501-65-5 ]
  • 5,6-diphenylbenzo[4,5]imidazo[2,1-a][2,6]naphthyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With {(η5-pentamethylcyclopentadienyl)cobalt(I)2}2; silver(I) acetate; sodium acetate In 2,2,2-trifluoroethanol at 60℃; for 12h; Inert atmosphere;
  • 41
  • [ 2208-59-5 ]
  • [ 1351282-86-4 ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide; p-toluenesulfonic acid monohydrate In tetrachloromethane at 65℃; for 20h; 1; 2; 3 Example 1 The compound for treating gastric cancer is prepared by a one-pot method.The one-pot method specifically includes the following steps: weighing 170 mg of 2-(4-pyridyl)benzimidazole, adding 15 mL of a carbon tetrachloride solvent, 5 mg of p-toluenesulfonic acid monohydrate, and 172 mg.N-bromosuccinimide,Heat to 65 ° C for 20 h,The solvent was removed by rotary evaporation, and then 115 mg of 7-bromoindazole was added.26.5 to 36.5 mg of dichloro(pentamethylcyclopentadienyl) ruthenium (III),Then dissolve together in 10 mL of anhydrous toluene.Add 0.05 mL of ethylenediamine dropwise while stirring, and then add 1 mg of cesium carbonate.4mL of triethylamine, then nitrogen gas for 30min,Add 10 mg of tetrakis(triphenylphosphine)palladium, 1.4 mg of CuI,45 mg of propynyl p-toluenesulfonate, heated to 70 ° C for 22 h,Hydrochloric acid was added dropwise until the solution was neutral, and an orange solid precipitated.That is, the compound for treating gastric cancer.
  • 42
  • dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer [ No CAS ]
  • [ 2208-59-5 ]
  • [ 126422-57-9 ]
  • [ 53857-58-2 ]
  • dichloro(2-pyridyl-5-diethylene glycol bis(2-propynyl)ether-1-indazolylbenzimidazolyl)pentamethylcyclopentadienylrhodium(III) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(pyridin-4-yl)-1H-benzo[d]imidazole With N-Bromosuccinimide; toluene-4-sulfonic acid In tetrachloromethane for 24h; Reflux; Stage #2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; α,ω-bis(O-propargyl)diethylene glycol; 7-bromo-1H-indazole With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); caesium carbonate; ethylenediamine; triethylamine In toluene at 80℃; for 24h; 1; 2; 3 Example 2 The above organic ruthenium complex is prepared by a one-pot method, and specifically includes the following steps:Weigh 175 mg of 2-(4-pyridyl)benzimidazole, add 20 mL of carbon tetrachloride solvent, 10 mg of p-toluenesulfonic acid monohydrate,177 mg of N-bromosuccinimide, heated to reflux for 24 h,The solvent was removed by rotary evaporation, and 120 mg of 7-bromocarbazole was added.35mg dichloro (pentamethylcyclopentadienyl yl) rhodium (III) dimer,Then dissolved in 15 mL of anhydrous toluene, and 0.1 mL of ethylenediamine was added dropwise while stirring, and then 3 mg of cesium carbonate was added.6mL of triethylamine, then nitrogen gas for 30min, adding 15mg of tetrakis(triphenylphosphine)palladium, 1.9mg of CuI,62 mg of diethylene glycol bis(2-propynyl)ether, heated to 80 ° C for 24 h,Orange solid was precipitated, that is a dichloro (2-pyridyl-5-glycol bis(2-propynyl)etheryl-1-oxazolylbenzimidazolyl)monopentamethylcyclopentadienylrhodium (III).
  • 43
  • [ 2208-59-5 ]
  • 2-(3-iodopyridin-4-yl)-1H-benzo[d]imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With [bis(acetoxy)iodo]benzene; iodine; palladium diacetate In acetonitrile at 80℃; for 3h; regioselective reaction;
  • 44
  • N-(2-aminophenyl)pyridine-4-carboxamide [ No CAS ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
66% With acetic acid at 120℃; General Method D (acid-catalysed cyclisation) General procedure: The corresponding amide (1 eq.) was dissolved in acetic acid (excess ca. 140 eq.) and heated to 120 °C. The reaction was monitored by TLC and after 1.5 h, all of the starting material had been consumed. The product was isolated as per specification.
  • 45
  • [ 504-29-0 ]
  • [ 50-00-0 ]
  • [ 2208-59-5 ]
  • N-((2-(pyridin-4-yl)-1H-benzo[d]imidazol-1-yl)methyl)pyridin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: formaldehyd; 2-(pyridin-4-yl)-1H-benzo[d]imidazole In methanol at 5 - 10℃; for 0.166667h; Stage #2: 2-aminopyridine In methanol at 5 - 10℃; for 1h; Stage #3: In methanol at 60 - 65℃; Microwave irradiation; General procedure for synthesis of (3a-e) & (4a-e) General procedure: Benzo[d]imidazole (1) or (2) (1.0 mmol) was dissolved in methanol (10 vol). To this solution, 0.19 mL 37% formaldehyde was added and stirred at 5-10 °C for about 10 min. Then a solution of substituted aminopyridine (1.0 equiv) in methanol (10 vol) was added dropwise to resulting reaction mixture at the same temperature with vigorous stirring for 1 h. The reaction mixture was then introduced to the microwave oven and was irradiated for 8-9 min at 60-65 °C (300 W) while monitoring the course of reaction by TLC (using dichloromethane: methanol, 9:11). Then after reaction mass was kept overnight at room temperature. The resulting solid was collected by filtration, washed with cold petroleum ether (2 X 2.5 mL), dried and recrystallized from ethanol to obtained pure (3a-e) & (4a-e). N-((2-(pyridin-4-yl)-1H-benzo[d]imidazol-1-yl)methyl)pyridin-2-amine (3a) Yield 87%, m.p. 218-220 °C, IR (KBr) ν cm-1: 3396 (N-H), 3055, 2936 (aromatic C-H), 2868 (methylene C-H, str.), 1606 (C=N), 1430 (methylene C-H, bend.), 1350 (C-N); 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.59 (t, 1H, NH, disappeared on D2O exchange), 8.32-7.71 (m, 4H, CH, aromatic; 4-pyridine), 7.46-7.08 (m, 8H, CH, aromatic; 2-pyridine & benzimidazole), 5.02 (d, 2H, CH2); 13C NMR (100 MHz, DMSO-d6) δ (ppm): (150.47; N-C=N), (149.78, 135.19, 121.43; 4-pyridine), (145.66, 140.75, 137.09, 123.67, 119.02; 2-pyridine), (122.58, 120.30, 118.53, 111.13, 106.79, 105.48; benzimidazole), 61.41 (CH2); ESI-MS: m/z calculated 301.13, found [M+H]+ 302.13; Anal.Calcd. for C18H15N5: C, 71.74; H, 5.02; N, 23.24. Found: C, 71.65; H, 4.93; N, 23.13%.
  • 46
  • [ 462-08-8 ]
  • [ 50-00-0 ]
  • [ 2208-59-5 ]
  • C18H15N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: formaldehyd; 2-(pyridin-4-yl)-1H-benzo[d]imidazole In methanol at 5 - 10℃; for 0.166667h; Stage #2: pyridin-3-ylamine In methanol at 5 - 10℃; for 1h; Stage #3: In methanol at 60 - 65℃; Microwave irradiation; General procedure for synthesis of (3a-e) & (4a-e) General procedure: Benzo[d]imidazole (1) or (2) (1.0 mmol) was dissolved in methanol (10 vol). To this solution, 0.19 mL 37% formaldehyde was added and stirred at 5-10 °C for about 10 min. Then a solution of substituted aminopyridine (1.0 equiv) in methanol (10 vol) was added dropwise to resulting reaction mixture at the same temperature with vigorous stirring for 1 h. The reaction mixture was then introduced to the microwave oven and was irradiated for 8-9 min at 60-65 °C (300 W) while monitoring the course of reaction by TLC (using dichloromethane: methanol, 9:11). Then after reaction mass was kept overnight at room temperature. The resulting solid was collected by filtration, washed with cold petroleum ether (2 X 2.5 mL), dried and recrystallized from ethanol to obtained pure (3a-e) & (4a-e).
  • 47
  • [ 504-24-5 ]
  • [ 50-00-0 ]
  • [ 2208-59-5 ]
  • C18H15N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: formaldehyd; 2-(pyridin-4-yl)-1H-benzo[d]imidazole In methanol at 5 - 10℃; for 0.166667h; Stage #2: 4-aminopyridine In methanol at 5 - 10℃; for 1h; Stage #3: In methanol at 60 - 65℃; Microwave irradiation; General procedure for synthesis of (3a-e) & (4a-e) General procedure: Benzo[d]imidazole (1) or (2) (1.0 mmol) was dissolved in methanol (10 vol). To this solution, 0.19 mL 37% formaldehyde was added and stirred at 5-10 °C for about 10 min. Then a solution of substituted aminopyridine (1.0 equiv) in methanol (10 vol) was added dropwise to resulting reaction mixture at the same temperature with vigorous stirring for 1 h. The reaction mixture was then introduced to the microwave oven and was irradiated for 8-9 min at 60-65 °C (300 W) while monitoring the course of reaction by TLC (using dichloromethane: methanol, 9:11). Then after reaction mass was kept overnight at room temperature. The resulting solid was collected by filtration, washed with cold petroleum ether (2 X 2.5 mL), dried and recrystallized from ethanol to obtained pure (3a-e) & (4a-e).
  • 48
  • [ 1603-41-4 ]
  • [ 50-00-0 ]
  • [ 2208-59-5 ]
  • C19H17N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: formaldehyd; 2-(pyridin-4-yl)-1H-benzo[d]imidazole In methanol at 5 - 10℃; for 0.166667h; Stage #2: (5-methyl-pyridin-2-yl)amine In methanol at 5 - 10℃; for 1h; Stage #3: In methanol at 60 - 65℃; Microwave irradiation; General procedure for synthesis of (3a-e) & (4a-e) General procedure: Benzo[d]imidazole (1) or (2) (1.0 mmol) was dissolved in methanol (10 vol). To this solution, 0.19 mL 37% formaldehyde was added and stirred at 5-10 °C for about 10 min. Then a solution of substituted aminopyridine (1.0 equiv) in methanol (10 vol) was added dropwise to resulting reaction mixture at the same temperature with vigorous stirring for 1 h. The reaction mixture was then introduced to the microwave oven and was irradiated for 8-9 min at 60-65 °C (300 W) while monitoring the course of reaction by TLC (using dichloromethane: methanol, 9:11). Then after reaction mass was kept overnight at room temperature. The resulting solid was collected by filtration, washed with cold petroleum ether (2 X 2.5 mL), dried and recrystallized from ethanol to obtained pure (3a-e) & (4a-e).
  • 49
  • [ 50-00-0 ]
  • [ 2208-59-5 ]
  • [ 391906-83-5 ]
  • C24H19N5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: formaldehyd; 2-(pyridin-4-yl)-1H-benzo[d]imidazole In methanol at 5 - 10℃; for 0.166667h; Stage #2: 2-amino-3-phenoxypyridine In methanol at 5 - 10℃; for 1h; Stage #3: In methanol at 60 - 65℃; Microwave irradiation; General procedure for synthesis of (3a-e) & (4a-e) General procedure: Benzo[d]imidazole (1) or (2) (1.0 mmol) was dissolved in methanol (10 vol). To this solution, 0.19 mL 37% formaldehyde was added and stirred at 5-10 °C for about 10 min. Then a solution of substituted aminopyridine (1.0 equiv) in methanol (10 vol) was added dropwise to resulting reaction mixture at the same temperature with vigorous stirring for 1 h. The reaction mixture was then introduced to the microwave oven and was irradiated for 8-9 min at 60-65 °C (300 W) while monitoring the course of reaction by TLC (using dichloromethane: methanol, 9:11). Then after reaction mass was kept overnight at room temperature. The resulting solid was collected by filtration, washed with cold petroleum ether (2 X 2.5 mL), dried and recrystallized from ethanol to obtained pure (3a-e) & (4a-e).
  • 50
  • [ 2208-59-5 ]
  • [ 51294-20-3 ]
YieldReaction ConditionsOperation in experiment
80% With sulfuric acid; dihydrogen peroxide at 139.84℃; for 1h;
  • 51
  • [ 148-24-3 ]
  • [ 14285-68-8 ]
  • [ 2208-59-5 ]
  • C24H15N4O4Re [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% In toluene; at 160℃; for 24.0h;High pressure; A mixture of Re 2 (CO) 10 (100.8 mg, 0.1544 mmol), 8-hydroxyquinoline (44.5 mg, 0.3065 mmol), 2-(4 - pyridyl)benzimidazole (59.8 mg, 0.3065 mmol) and toluene (10 mL) was taken in a Teflon flask that was placed in a steel bomb. The bomb was kept in an oven maintained at 160 C for 24 h and then cooled to 25 C. Good quality, yellow single crystals of 1 were obtained. Yield: 69% (130.3 mg). Anal. Calcd for C 24 H 15 N 4 O 4 Re.C 7 H 8 : C, 52.24; H, 3.36; N, 8.12. Found: C, 51.13; H, 3.03; N, 7.77. IR (KBr, cm -1 ): 2019 (C O), 1911 (C O), 1890 (C O). 1 H NMR (500 MHz, DMSO- d 6 , ): mixture of two isomers with 1: 0.9 ratio without solvent toluene molecule: 9.19 (dd, J = 4.88 and 1.35 Hz, H a ), 8.96 (dd, J = 4.82 and 1.37 Hz, H a ), 8.77-8.74 (m, H 9 ), 8.54 (dd, J = 7.19 and 1.33 Hz, H c ), 8.46 (dd, J = 7.19 and 1.35 Hz, H c ), 8.10-8.09 (m, H 8 ), 8.06-8.05 (m, H 8 ), 7.66-7.60 (br and m, H d , H 4 , H 7 ), 7.47 (t, J = 7.92 Hz, H b ), 7.39 (t, J = 7.95 Hz, H b ), 7.28-7.25 (b and m, H 5-6 ), 7.09 (dd, J = 8.08 and 0.89 Hz, H e ), 6.99 (dd, J = 7.19 and 0.89 Hz, H e ), 6.95 (dd, J = 7.92 and 0.99 Hz, H f ), and 6.91 (dd, J = 7.84 and 0.99 Hz, H f ).
  • 52
  • [ 3731-53-1 ]
  • [ 1493-27-2 ]
  • [ 2208-59-5 ]
YieldReaction ConditionsOperation in experiment
59% With 1-methyl-pyrrolidin-2-one; potassium carbonate at 225℃; for 4h; Microwave irradiation; General procedure: To a 10-20 mL capacity microwave vial was added 1-fluoro-2- nitrobenzene (0.400 g, 2.830 mmol, 1 equiv.), benzylamine (0.330 g, 3.120 mmol, 1.1 equiv.) and potassium carbonate (0.978 g, 7.092 mmol, 2.5 equiv.) in N-methylpyrrolidone (15 mL). The vial was properly closed and irradiated in microwave reactor at 225 C for 4 h. The vial was then cooled to ambient temperature and water (30 mL) was added to it, followed by extraction with ethyl acetate (200 mL). The organic extract was washed with water (150 mL), brine (25 mL), and dried over anhydrous sodium sulfate. Subsequently, it was filtered and concentrated to obtain a dark brown sticky mass. The crude material obtained was loaded on a pre packed silica gel 50 g SNAP cartridge and purified by flash chromatography on a Biotage instrument using 50-60% gradient of ethyl acetate in hexane to obtain pure 2- phenyl-1H-benzo[d]imidazole as a light brown solid (0.358 g, 65%).
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