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CAS No. : | 1632-83-3 | MDL No. : | MFCD00192275 |
Formula : | C8H8N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FGYADSCZTQOAFK-UHFFFAOYSA-N |
M.W : | 132.16 | Pubchem ID : | 95890 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With ammonium peroxydisulfate; caesium carbonate In dimethyl sulfoxide at 20℃; for 24 h; Inert atmosphere; Irradiation; Green chemistry | General procedure: Heterocycle (0.10mmol,1equiv)ammonium persulfate (0.30 mmol, 3 equiv), Cs2CO3(0.20mmol,2 equiv)were placed in a dry glass tube.Then, anhydrous DMSO1 mL) and2,2-diethoxyacetic acid (0.7mmol7equiv), wereinjected into the tube by syringe under a N2atmosphere.The solution was then stirred at roomtemperature under the irradiation of 15W blueLEDs strip for 24h.After completion of the reaction,the mixture was quenched by addition of1.2mL of 3.0 M HCl, stirred for 20hthen saturated Na2CO3solution was added to adjust pH tobasicextract with CH2Cl2,the combined organic layers was washed with brine, then dry overanhydrous Na2SO4. The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum and ethylacetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With hydrogenchloride; n-butyllithium; carbon dioxide In diethyl ether; water | EXAMPLE 375A 1-methyl-1H-benzimidazole-2-carboxylic acid A suspension of 1-methyl-1H-benzimidazole (5.0 g, 37.83 mmol) in diethyl ether at -78° C. was treated slowly with 1.6M n-butyllithium in hexanes (26 mL, 41.61 mmol) while maintaining the temperature at below -60° C., and stirred at -78° C. for 30 minutes. Carbon dioxide was bubbled through the reaction solution for 40 minutes. The dry ice bath was then removed to bring the temperature to -5° C. Concentrated hydrochloric acid (7 mL) was added slowly. The reaction mixture was stirred at -5° C. for 30 minutes, and then water (10 mL) was added. The solid was collected by filtration and dried to remove the excess water to provide 4.8 g (72percent) of the desired product which was directly used in the next reaction without further purification or analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: With 3-benzyl-1-(1-((2,6-diisopropylphenyl)imino)ethyl)-1H-imidazol-3-ium chloride; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 80℃; for 24 h; Inert atmosphere Stage #2: at 65℃; for 1 h; Inert atmosphere |
In the reaction flask, Under argon, a catalyst (9.9 mg, 0.025 mmol, 5 molpercent), potassium tert-butoxide (0.0672 g, 0.6 mmol) DMF (3.0 ml), 1-methylbenzimidazole (60.0 μl, 0.5 mmol) was added to the carbon dioxide gas, and the reaction was stirred at 80 ° C for 24 hours under normal pressure. Cooled to 65 ° C, methyl iodide (93 μl, 1.5 mmol) was added, The reaction was stirred at 65 ° C for 1 hour. Cooled to room temperature, the reaction was terminated with deionized water, The reaction product was extracted with ethyl acetate and purified by column chromatography (Using a mixed solvent of ethyl acetate / petroleum ether in a volume ratio of 1:10 as a developing solvent) The yield was 50percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With sodium hydroxide; In water; at 20℃; for 1h; | N-Methylimidazole, quinoline, benzimidazole, iodomethaneand anhydrous NiBr2 were purchased from Sigma-Aldrich (>99%)and used as received. N-Methyl-benzimidazole was synthesizedaccording to a known literature method [10]: Benzimidazole (25.0 g, 211.6 mmol) is added in one portion to 100 mL of a stirred ice-cold 50% aqueous NaOH solution. Iodomethane (33.0 g, 232.8 mmol) is added dropwise under vigorous stirring to the clear benzimidazole solution at ambient temperature. After 1 h the solution is extracted three times with 100 mL portions of chloroform. The combined organic phases are dried with Na2SO4 and the solvent is removed under reduced pressure. The residue is distilled in vacuo, yielding N-methyl-benzimidazole as a colorless liquid, which solidifies upon cooling. Yield: 21.0 g (75%), mp. 61 C. Elemental anal. % (calc. for C8H8N2): C, 72.50 (72.70); H, 6.19 (6.10); N, 21.18 (21.20). |
71% | KO(t-Bu) (1.04 g, 9.31 mmol) was added all at once, as a solid, to a stirring solution ofbenzimidazole (1.00 g, 8.46 mmol) in THF (50 mL), affording a white precipitate. The cloudy,white mixture was allowed to stir for 1 h, after which time MeI (1.05 mL, 16.93 mmol) was addeddropwise via syringe, with no apparent change. After the addition, the mixture was allowed to stirfor 1 h, after which time the volatiles were removed under reduced pressure, yielding a white solid.The solid was extracted into CH2Cl2 (2 × 30 mL) and filtered through Celite. The volatiles wereremoved from the clear, light yellow filtrate, yielding a yellow liquid. Yield: 0.790 g (71%). | |
With potassium hydroxide; In ethanol; water; | STEP A: 1-methyl-benzimidazole 14.1 g of methyl iodide and 6.15 g of potassium hydroxide were added to a suspension of 11.8 g of benzimidazole in 50 ml of ethanol and 30 ml of water and the mixture was refluxed for 6 hours and was then cooled. The mixture was extracted three times with chloroform and the combined chloroform extracts were dried and filtered. The filtrate was evaporated to dryness and the oily residue was chromatographed over neutral alumina. Elution with chloroform yielded 1-methyl-benzimidazole as a crude oil which was used as is for the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With polymeric resin-bound hexafluorophosphate ion; In methanol; water; at 20℃; for 8h; | General procedure: In a typical experimental procedure, o-phenlylenediamine and benzaldehyde in 1:2 molar ratios was taken in a 100 ml round bottom flask. To this water-methanol (1:1) and 100 mg PHP was admixed. The reaction mixture was then allowed to stir with magnetic spinning bar, after some time a yellowish mass appeared which settles down like a precipitate after the completion of the reaction (checked by TLC). It was then filtered; the solid reaction mixture was dissolved with dichloromethane (25 mL) and evaporated under vacuum. The crude product was then crystallised from ethanol. The desired product was pure on TLC and characterized by spectral (IR, 1H and 13C NMR) data and compared to those reported in literature. |
68% | With polymeric resin-bound hexafluorophosphate ion; In methanol; water; at 20℃; for 8h; | General procedure: In a typical experimental procedure, o-phenlylenediamine and benzaldehyde in 1:2 molar ratios was taken in a 100 ml round bottom flask. To this water-methanol (1:1) and 100 mg PHP was admixed. The reaction mixture was then allowed to stir with magnetic spinning bar, after some time a yellowish mass appeared which settles down like a precipitate after the completion of the reaction (checked by TLC). It was then filtered; the solid reaction mixture was dissolved with dichloromethane (25 mL) and evaporated under vacuum. The crude product was then crystallised from ethanol. The desired product was pure on TLC and characterized by spectral (IR, 1H and 13C NMR) data and compared to those reported in literature. |
68% | With sodium dodecyl-sulfate; In water; at 20℃; for 8h;Green chemistry; | General procedure: In a typical experimental procedure, o-phenylelenediamine and benzaldehyde in 1:2 molar ratios was taken in a 100 ml round bottom flask. To this water and 10 mg sodium dodecyl sulfate was admixed. The reaction mixture was then allowed to stir at room temperature with magnetic spinning bar. A foamy mass appeared immediately and get settled like a precipitate. After the completion of the reaction, the solid reaction mixture was washed with dichloromethane (5×4`) and the washings were collected and evaporated under vacuum. The crude product was then crystallized from ethanol. The desired purified product was characterized by spectral (IR, 1H and 13C NMR) data and compared to those reported in literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With N-Bromosuccinimide; In tetrahydrofuran; for 1h;Reflux; | 1-rnethylbenzimidazole (11) (5.0 g, 37.8 mrnol) and N-bromosuccinimide (20.2 g, 113.5 mmol) in 200 mL of THF was heated under reflux for I h. The solvent was removed in rotary evaporator and the residue was recrystallized from EtOAc yielding 8 (7.4 g, 93%) as a white solid. ?H NMR (DMSO-d6) 6 7.77 (d, 1H), 7.65 (d, IH), 7.39 (m, 2H), 3.86 (s, 3H); ?3C NMR (DMSOd5) 6 138.2, 135.4, 131.5, 124.8,124.7, 117.0, 112.3, 33.0; HRMS (ESIQTOF): ni/z Calcd for C8H7N2Br + H: 210.9871, found: 210.9911. |
85% | With carbon tetrabromide; sodium t-butanolate; In N,N-dimethyl-formamide; at 20℃; for 3h; | 1-methylbenzimidazole (1 mmol, 132.1 mg)Carbon tetrabromide (1.1 mmol, 364.8 mg) was placed in a 10 mL round bottom flask.Add 5 mL of N,N-dimethylformamideSodium tert-butoxide (4.0 mmol, 384.4 mg),Stir at room temperature for 3 hours,TLC monitored the endpoint of the reaction.The mixture was poured into water and extracted with dichloromethane. The organic phase was collected and dried. The dichloromethane was removed by rotary evaporation to give the crude product.The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (ratio by volume = 15:1).2-Bromo-1-methylbenzimidazole was obtained (white solid, 179.0 mg, yield 85%). |
41% | Under inert atmosphere, N-methylbenzimidazole (2.90 g, 17.3 mmol, 1.00 equiv.) was dissolvedin THF (90 mL) and cooled to -78 C. Within 20 minutes a solution of n-butyl lithium inn-hexane (16.5 ml, 1.6 M, 26 mmol, 1.5 equiv.) was added dropwise and the solution was stirredfor an additional hour. Tetrabromomethane (9.79 g, 29.5 mmol, 1.71 equiv.) dissolved in THF(60 mL) was added dropwise within 1 hour and stirred for 1 additional hour while warm up toroom temperature. A saturated aqueous NH4Cl-solution (100 mL) was added, and the mixturewas extracted with ethyl acetate (3×70 mL). The combined organic layers were dried overMgSO4 and the solvent was evaporated. The crude product was purified by columnchromatography (silica; ethyl acetate/cyclohexane 1:2.5 v/v) to afford the desired product as ayellow solid (1.49 g, 7.06 mmol, 41 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With copper(II) oxide; potassium carbonate; triphenylphosphine; In diethylene glycol dimethyl ether; at 160℃; for 24h;Reflux; Inert atmosphere; Sealed tube; | General procedure: 4.3 General procedure for CuO-catalyzed arylation and alkenylation of 1,3-azole (0012) Under argon, 0.5mmol of the bromobenzene or bromoalkene was added to the reaction mixture containing 0.25mmol of the benzoxazole, 0.5mmol K2CO3, 0.025mmol CuO, and 0.075mmol PPh3, followed by the addition of 2mL dry diglyme. The sealed reaction tube was stirred at 160°C for 5?24h. After cooling, the reaction mixture was centrifuged to remove solid and separated the organic phase. Then, organic phase was extracted and dried over anhydrous MgSO4, and concentrated under reduced pressure after filtered. The residue was purified by column chromatography on silica gel eluted to afford corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 10 molpercent nickel based 2,5-dihydroxyterephthalic acid metal organic framework-74; In diethylene glycol dimethyl ether; at 160℃; for 18h;Sealed tube; | General procedure: In a typical experiment, a predetermined amount of Ni-MOF-74 was added to the 8 mL vial containing a mixture of iodobenzene (0.1030 g, 0.5 mmol), benzothiazole (0.1379 g, 1.0 mmol), Li2CO3 or KCl (1.0 mmol), and diphenyl ether (0.085 g, 0.5 mmol) as standard. 1-Methoxy-2-(2-methoxyethoxy)ethane (diglyme) (1 mL) was added and vial was tightly capped. Reaction mixture was heated at 160°C for 24 h. The catalyst loading was based on the molar ratio of nickel/iodobenzene. The reaction yield was monitored by withdrawing aliquots from the reaction mixture at different time intervals, diluting with ethylacetate (2 mL), quenching with an aqueous KOH solution (1percent, 1 mL), and then drying over anhydrous Na2SO4 before analyzing by GC with reference to diphenyl ether (internal equation with pure product), and further confirming product identity by GC?MS and NMR. To investigatethe recycle ability of Ni-MOF-74, the catalyst was filtered from the reaction mixture after the experiment, washed with ethylacetate, water, THF, and dried at 140°C under vacuum in 8 h. For the leaching test, a catalytic reaction was stopped after 12 h, analyzed by GC, and filtered to remove the solid catalyst. The reaction solution was then stirred for a further 12 h. Reaction progress, if any, was monitored by GC as previously described. |
67% | With (1-(2-(tert-butylamino)ethyl)-3-mesityl-2,3-dihydro-1H-imidazol-2-yl)copper(I) iodide; lithium tert-butoxide; In N,N-dimethyl-formamide; at 140℃; for 8h;Glovebox; | General procedure: The product 12a is a representative reaction. To a vial (5 mL) containing caffeine (0.5 mmol), iodobenzene (1.0 mmol), catalyst 3e (0.05 mmol), and LiOtBu (1.0 mmol) was added DMF (1.0 mL) solvent under a glovebox atmosphere. After the substances were completely dissolved, the vial was screw-capped, taken outside the glovebox and heated at 140 °C for 8 h. The resulting mixture was filtered through Celite and washed with dichloromethane. The filtrate solution was concentrated in vacuo to afford the crude product, which was further purified by column chromatography using hexane/ethyl acetate as eluent to furnish 12a in 80percent yield. |
46% | With potassium phosphate; Cu2(4,4?-biphenyldicarboxylate)2(4,4?-bipyridine); In Hexadecane; N,N-dimethyl-formamide; at 120℃; for 3h;Green chemistry; | General procedure: In a typical experiment, a pre-determined amount of Cu2(BPDC)2(BPY) was added to theflask containing a solution of iodobenzene (0.112 mL, 1 mmol),benzoxazole (0.238 g, 2 mmol), K3PO4(0.532 g, 2 mmol) and n-hexadecane (0.1 mL) as internal standard in DMF (4 mL). Thecatalyst concentration was calculated based on the molar ratio ofcopper/iodobenzene. The reaction mixture was stirred at 100Cunder an argon atmosphere for 180 min. The reaction conver-sion was monitored by withdrawing aliquots from the reactionmixture at different time intervals, quenching with an aqueousNaOH solution (5percent, 1 mL), drying over anhydrous Na2SO4, analyz-ing by GC with reference to n-hexadecane, and further confirmingproduct identity by GC?MS. To investigate the recyclability ofCu2(BPDC)2(BPY), the catalyst was filtered from the reaction mix-ture after the experiment, washed with copious amounts of DMF,dried under air at room temperature for 1 h, and reused if neces-sary. For the leaching test, a catalytic reaction was stopped after30 min, analyzed by GC, and filtered to remove the solid catalyst.The reaction solution was then stirred for a further 150 min. Reac-tion progress, if any, was monitored by GC as previously described. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium amide In xylene | ||
Multi-step reaction with 3 steps 1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C 1.2: 27 percent / hexane; tetrahydrofuran / 0.5 h / -78 °C 2.1: 31.4 percent / H2N-NH2*H2O / ethanol / Heating 3.1: NaNO2; conc. HCl / H2O / 1 h / 20 °C 3.2: 56.3 percent / conc. HCl / 1 h / 80 °C | ||
Multi-step reaction with 2 steps 1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C 1.2: 90 percent / tosyl azide / tetrahydrofuran / 0.5 h 2.1: 89.5 percent / H2 / 10 percent Pd-C / ethanol / 3 h / 20 °C |
Multi-step reaction with 2 steps 1: LDA 2: 25.1 percent / H2 / PtO2 / trifluoroacetic acid | ||
Multi-step reaction with 3 steps 1: 73.5 percent / NBS 2: 80.9 percent / NaN3 / PdCl2(PPh3)2 / tetrahydrofuran; H2O / 48 h / 60 °C 3: 89.5 percent / H2 / Pd-C | ||
Multi-step reaction with 2 steps 1: 73.5 percent / NBS 2: 30.6 percent / aq NH3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane; potassium tert-butylate; In toluene; at 20℃; for 3h; | 1-methylbenzimidazole (1 mmol, 132.1 mg)Perfluoroiodobutane (1.1 mmol, 380.5 mg) was placed in a 10 mL round bottom flask.Potassium tert-butoxide (1.2 mmol, 134.7 mg) is addedAnd 5mL of toluene,Stir at room temperature for 3 hours,TLC monitored the endpoint of the reaction.After the toluene was removed by rotary evaporation, the mixture was washed with water and extracted with dichloromethane. The organic phase was collected and dried. The dichloromethane was removed by rotary evaporation to give a crude product.The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluents (ratio by volume = 15:1).2-Iodo-1-methylbenzimidazole was obtained (white solid, 208.9 mg, yield 81%). |
53% | Under inert atmosphere, N-methylbenzimidazole (1.00 g, 7.57 mmol, 1.00 equiv.) was dissolvedin THF (30 mL) and cooled to -78 C. During a period of 20 minutes a solution of n-butyllithium in n-hexane (5.68 mL, 1.60 M, 9.09 mmol, 1.20 equiv.) was added dropwise. Thesolution was stirred for 1 hour and iodine (2.50 g, 9.84 mmol, 1.30 equiv.) dissolved in THF(20 mL) was added dropwise within 1 hour and was stirred for an additional hour while warmingup to room temperature. The mixture was deactivated with saturated aqueous Na2S2O3-solution(50 mL) and saturated aqueous NH4Cl-solution (50 mL) and was extracted with dichloromethane(3×50 mL). The combined organic layers were dried with MgSO4. Removal of the solventfollowed by purification by column chromatography (silica; ethyl acetate/cyclohexane 1:2 v/v;Rf = 0.38) gave the desired product as white solid (1.03 g, 3.99 mmol, 53 %). | |
21% | In an oven dried nitrogen purged 3 neck 100 mL round bottom flask, 1.00 g (7.57 mmol) of 1 -methylbenzimidazole in 20 mL of dry tetrahydrofuran is cooled to -78C. 10.69 mL (18.17 mmol) of 1.7 M t-butyllithium in hexanes is added and the reaction mixture is stirred at -780C. for 1 h. 2.55 g (11.36 mmol) of NIS in 20 mL of dry tetrahydrofuran is added. Reaction is removed from bath and stirred at room temperature for 1 hour, quenched with saturated aqueous solution of ammonium chloride, and diluted with dichloromethane. The layers are separated, the aqueous is extracted 3X100 mL dichloromethane, dried (MgSO4), and concentrated. The crude mixture is purified by EPO <DP n="53"/>chromatography using hexanes:ethyl acetate as a solvent system. The product containing fractions are combined to obtain 0.400 g of the title compound, 21% yield. MS, ES+ = 259.0 (M+l); 1H NMR (DMSO-d6) 57.580-7.552 (m, 2H); 7.228-7.129 (m, 2H); 3.750 (s, 3H) ppm. |
15% | With 1,10-Phenanthroline; iodine; copper(ll) bromide; lithium tert-butoxide; In 1,4-dioxane; at 80℃;Inert atmosphere; | General procedure: To a flame-dried reaction tube was added 1,3-azoles (0.5 mmol, 1.0 eq), 1,10-phenoline (0.5 mmol, 1.0 eq), LiOtBu (1.0 mmol, 2.0 eq), CuBr2 (0.10 mmol, 0.2 eq) and iodine (0.75 mmol, 1.5 eq). Dry 1,4-dioxane (2 mL) was added to the mixture and the mixture was heated to 80C by putting the reaction tube to a preheated oil bath until the products were not increased. The mixture was cooled to room temperature and filtered through a short pad of silica gel. The silica gel was washed with EtOAc (20 mL) and the combined the organic phase was concentrated under reduced pressure to give a residue which was purified by silica gel column chromatography to afford the iodination product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With copper acetylacetonate; oxygen; In 5,5-dimethyl-1,3-cyclohexadiene; at 140℃; for 20h; | General procedure: In a 25 mL two necked round bottom flask, azole (1 mmol), amine (2.0 mmol), Cu(acac)2 (52.6 mg, 20 mol %), and 5 mL xylene were added. The above mixture was kept under reflux condition and then molecular oxygen was bubbled into the reaction mixture till the completion of reaction. The progress of reaction was monitored using gas chromatography. After completion of the reaction, the reaction mixture was filtered through celite bed. The organic solvent was removed under reduced pressure. The reaction mixture was analyzed using gas chromatography (Perkin Elmer, Clarus 400) equipped with a flame ionization detector (FID) and capillary column. The crude product was purified by column chromatography (silica gel, 100-200 mesh; petroleum ether/ethyl acetate, 90:10) to afford pure products. All the prepared compounds were confirmed by comparing with their authentic samples and were characterized by GC-MS (Shimadzu QP 2010), 1H NMR (Varian 500 MHz). |
51% | With oxygen; copper diacetate; sodium acetate; triphenylphosphine; In 5,5-dimethyl-1,3-cyclohexadiene; at 140℃; for 20h; | General procedure: A solution of copper(II) acetate (7.3 mg, 0.04 mmol), triphenylphosphine (21 mg, 0.08 mmol), benzothiazole (1, 22 muL, 0.2 mmol), N-methylaniline 2a (0.088 mL, 0.8 mmol) and NaOAc (66 mg, 0.8 mmol) in 1.0 mL of xylene was stirred at 140 C for 20 h under O2. After cooling to room temperature, the mixture was passed through a Celite pad, which was washed with chloroform repeatedly. The filtrate was washed with water three times. The organic layer was concentrated under reduced pressure to leave a crude oil, which was purified by column chromatography on silica gel to afford 39 mg of 3a as a colourless oil (75%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 55% 2: 40% | With pyridine; oxygen; copper diacetate; sodium carbonate In toluene at 20℃; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With pyridine; oxygen; copper diacetate; sodium carbonate In toluene at 20℃; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper(II) oxide; potassium carbonate; triphenylphosphine; In diethylene glycol dimethyl ether; at 160℃; for 24h;Reflux; Inert atmosphere; Sealed tube; | General procedure: 4.3 General procedure for CuO-catalyzed arylation and alkenylation of 1,3-azole (0012) Under argon, 0.5mmol of the bromobenzene or bromoalkene was added to the reaction mixture containing 0.25mmol of the benzoxazole, 0.5mmol K2CO3, 0.025mmol CuO, and 0.075mmol PPh3, followed by the addition of 2mL dry diglyme. The sealed reaction tube was stirred at 160C for 5-24h. After cooling, the reaction mixture was centrifuged to remove solid and separated the organic phase. Then, organic phase was extracted and dried over anhydrous MgSO4, and concentrated under reduced pressure after filtered. The residue was purified by column chromatography on silica gel eluted to afford corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | A mixture of <strong>[153034-94-7]2-fluoro-4-iodo-5-methylpyridine</strong> (1.52 g, 6.29 mmol), 1 -methyl benzimidazole (700 mg, 5.2 mmol), copper iodide (998 mg, 5.24 mmol), triphenyl phosphine (275 mg, 1 .05 mmol) and sodium carbonate (1.1 1 g, 10.5 mmol) in DMSO (20 mL) under nitrogen was stirred at 160 C for 17 hours. The reaction mixture was cooled to room temperature and poured into a mixture of water (100 mL) and ethylenediamine (12 mL). The combined mixture was extracted with EtOAc (2 x 150 mL), washed with saturated NaCI solution (150 mL), dried with sodium sulfate, filtered and concentrated. The crude product was purified by flash column chromatography (40 g silica gel, 5-50 % EtOAc/Heptane) to provide the title compound (535 mg, 42 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With copper(II) oxide; potassium carbonate; triphenylphosphine; In diethylene glycol dimethyl ether; at 160℃; for 24h;Reflux; Inert atmosphere; Sealed tube; | General procedure: 4.3 General procedure for CuO-catalyzed arylation and alkenylation of 1,3-azole (0012) Under argon, 0.5mmol of the bromobenzene or bromoalkene was added to the reaction mixture containing 0.25mmol of the benzoxazole, 0.5mmol K2CO3, 0.025mmol CuO, and 0.075mmol PPh3, followed by the addition of 2mL dry diglyme. The sealed reaction tube was stirred at 160C for 5-24h. After cooling, the reaction mixture was centrifuged to remove solid and separated the organic phase. Then, organic phase was extracted and dried over anhydrous MgSO4, and concentrated under reduced pressure after filtered. The residue was purified by column chromatography on silica gel eluted to afford corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In dichloromethane at 20℃; for 24h; Inert atmosphere; | 4.2. General procedure for the synthesis of imidazoles 4 General procedure: To a solution of acetylenic ketone 1 (1.0 mmol) and N-alkylimmidazole 3 (1.0 mmol) in DCM (5 mL) was slowly added isocyanate 2 (1.0 mmol) through a syringe under nitrogen atmosphere over 3-5 min. The reaction mixture was stirred at room temperature for 24 h. After the solvent was removed under reduced pressure, the residue was subject to flash chromatography on silica gel (petroleum ether/ethyl acetate, 2:1 to 1:1) to afford pure 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | In 1,4-dioxane; at 110℃; for 16h; | General procedure: To 1,4-dioxane were added azole derivative (0.293 M) and alpha-chloroacetamide derivative (0.267 M), which was prepared from chloroacetyl chloride and alpha-aminoester. After stirring the reaction mixture at 110 C for 16 h, the solvent was removed under reduced pressure. The residue was dissolved in methanol, and then activated carbon was added. After 16 h, the activated carbon was removed by filtration. The filtrate was concentrated under reduced pressure to obtain a solid, which was purified by reprecipitation using ethyl acetate and methanol to afford the corresponding azolium compound. Because of the highly hydroscopic character, elemental analyses of 1-4, 6-13, and 25 were not preformed. Azolium salts 7, 10, and 14-16 were reported in the preceding paper.12b Because of the light-sensitive character, elemental analyses of 28 and 29 were not preformed. |
86% | In toluene; at 100℃; under 760.051 Torr; for 3h;Sealed tube; | Step (2):Add 1-methylbenzimidazole (2 mmol) to a 35 mL pressure tube.Add toluene (4mL) at the same time,After being evenly dispersed,0.414 g (2.0 mmol) of the above crude methyl (S)-2-(2-chloroacetamido)-2,3-dimethylbutanoate was added.100 C, under a sealed condition of 1 atmosphere,The reaction was stirred at 800 r/min for 3 h. After the reaction is completed, the reaction bodyRotate dry,Add methylene chloride until the mixture just dissolves.Ethyl ether was added dropwise until white turbidity appeared.Move the system to -10 to 20 C,Cooling and crystallization, filtration,Eluate the filter cake with ether,Obtaining a beige or light yellow solid is 0.584 g of the azacarbene product, yield 86%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With C75H73Br2N2NiO5P; magnesium; In tetrahydrofuran; at 80℃; for 60h;Inert atmosphere; | Under argon atmosphere, the catalyst (66 mg, 0.05 mmol, 10 mol%) and magnesium turnings (12.0 mg, 0.5 mmol) were successively added to the reaction flask.N-methylbenzimidazole (66 mg, 0.5 mmol), styrene (86 mul, 0.75 mmol), tetrahydrofuran (1.5 ml) as a solvent, reacted at 80C for 60 hours, and quenched with water, the reaction product Extract with ethyl acetate,Purification by column chromatography (developing solvent in a mixed solvent of ethyl acetate/petroleum ether at a volume ratio of 1:20) gave a yield of 87%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With 3,4,7,8-Tetramethyl-o-phenanthrolin; di-tert-butyl peroxide; copper(l) chloride In toluene at 100℃; for 12h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With dimethylamine borane; In water; at 100℃; under 18751.9 Torr; for 24h;Heating; Green chemistry; | General procedure: Synthesis of benzimidazole from o-phenylenediamine byCO2and DMAB in presence of Cu(at)U-g-C3N4 was carriedout in high pressure reactor equipped with an overheadstirrer. In a general experiment for the synthesis ofbenzimidazole, o-phenylenediamine (1.00mmol), DMAB(3mmol), PC:H2O (3 mL:1.5mL), Cu(at)U-g-C3N4 (20mg)were loaded into the reactor at room temperature, reactorwas sealed, flushed three times with CO2and 2.5MPa CO2pressure was loaded in to reactor, heated to required temperaturewith stirring (600rpm). After completion of thereaction, the reactor was cooled to room temperature andthe pressure was slowly released. The catalyst was separatedby fltration, washed with ethyl acetate and water.The combined mixture was concentrated in vacuo and theproducts were purified by the column chromatographywith silica gel of 100-200 mesh size and petroleum etherethylacetate used as an eluent to aford pure products The spectroscopic data of all the products werematching with those reported in the literature. |
With N,N?-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride; In tetrahydrofuran; at 70℃; under 750.075 - 2250.23 Torr; for 24h;Schlenk technique; Inert atmosphere; Glovebox; | General procedure: A-Synthesis of Benzimidazole and Derivatives from Aromatic 1,2-DiaminesThe first results presented describe the synthesis of benzimidazole rings and derivatives from aromatic 1,2-diamines. In this case, the amine R1NH2 and the nitrogenous nucleophilic agent R5R6NH are two reactive functional groups of one and the same molecule (diamine) and are thus connected via a covalent bond. This bond is preferably an aromatic ring of benzene, pyridine or pyrimidine type and the ring formed during the reaction is a nitrogenous heterocycle comprising 5 atoms of imidazole type. In the case where the nucleophile is oxygen-based (R7OH), the rings obtained are benzoxazoles. The results presented were produced by preferably using two sources of different reducing agents, polymethylhydrosiloxane (PMHS), sold by Aldrich under the reference 176206, and phenylsilane (PhSiH3), sold by Aldrich. In the case of the PMHS, as a silane is a polymer, the number of equivalents introduced is given with respect to the number of hydrides introduced and thus the number of monomers introduced with respect to the amine. Thus, the introduction of 3 equivalents of PMHS corresponds to the introduction of 3 equivalents of hydride and thus 3 equivalents of monomers of the PMHS with respect to the amine. Different (pre)catalysts were tested for the reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With bis(1,5-cyclooctadiene)nickel(0); potassium tert-butylate; 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene; In toluene; at 80℃; for 2h;Inert atmosphere; Glovebox; | General procedure: The product 7h is a representative reaction. To a screw-cappedvial (5 mL) containing Ni(COD)2 (14 mg, 0.05 mmol), IMes (14 mg, 0.05 mmol),benzimidazole (66 mg, 0.50 mmol), and potassium tert-butoxide (5.6 mg, 0.05 mmol)was added toluene (1.0 mL) followed by the addition of 1,5-cyclooctadiene (43 mg,0.04 mmol) in a glove box atmosphere. The reaction vial was closed and heated at 80o C for 2 hours outside of the glove box. The resulting mixture was filtered throughCelite and washed with dichloromethane. The filtrate solution was concentrated invacuo to afford the crude product, which was further purified by columnchromatography using hexane/ethyl acetate (4:1 v/v) as eluent to furnish(E)-2-(cyclooctenyl)-1-methyl-benzimidazole 7h (117 mg) in 97% yield.The compound 7i was synthesized via similar conditions (see Table 3)._(E)-2-(cyclooct-1-en-1-yl)-1-methyl-1H-benzo[d]imidazole (7h): 1H NMR (300MHz, CDCl3): delta 7.75-7.71 (m, 1H), 7.25-7.19 (m, 3H), 6.06 (t, J = 8.1, 1H), 3.72 (s,3H), 2.75-2.71 (m, 2H), 2.36 (dd, J = 8.1, 11.4, 2H), 1.66-1.59 (m, 8H). 13C NMR (75MHz, CDCl3): delta 155.6, 142.4, 136.1, 135.8, 131.6, 122.1, 121.8, 119.3, 109.2, 31.6,29.3, 29.0, 28.9, 26.9, 26.4, 26.1. HR-MS (EI): calculated for: [C16H20N2]+: 240.1626.Found: 240.1620. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With iron(III) chloride; copper(II) acetate dihydrate; palladium dichloride; In N,N-dimethyl-formamide; at 120℃; for 24h; | General procedure: Azole (0.5 mmol), arylboronic acid (1.0 mmol), PdCl2(0.05 mmol), Cu(OAc)2·H2O (0.25 mmol), FeCl3 (0.25mmol) and DMF (2.0 mL) were taken in a 25 mL two-neckflask. The mixture was heated at 120 °C in air for 24 h bymagnetic stirring. After cooling to room temperature, theproduct was diluted with H2O (5 mL) and extracted withEtOAc (415 mL). The extracts were combined and washedby brine (310 mL), dried over MgSO4, filtered, and evaporated,and purified by chromatography on silica gel to obtainthe desired products with ethyl acetate/hexane(v/v=1:11:10). The products were characterized by theirspectral and analytical data and compared with those of theknown compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With perchloric acid; In diethyl ether; dichloromethane; water; at 0 - 20℃; for 3h; | Compound 4b (2.86 g, 91%) was obtained under the following conditions: 1-methylbenzimidazole (1.78 g, 14 mmol), 70% aqueous perchloric acid (1.16 mL, 14 mmol), CH2Cl2 (5.0 mL), Et2O (280 mL). Mp 120-121 C; [found: C, 41.14; H, 3.89; N, 12.00. C8H9ClN2O4 requires C, 41.31; H, 3.90; N, 12.04.]; IR (KBr) 3161, 1992, 1614, 1564, 1454, 1361, 1272 cm-1; 1H NMR (500 MHz, DMSO-d6) delta 4.08 (s, 3H), 7.64 (m, 2H), 7.87 (m, 1H), 7.99 (m, 1H), 9.54 (s, 1H); 13C NMR (125 MHz, DMSO-d6) delta 33.0, 113.2, 114.8, 126.0, 126.4, 130.8, 131.8, 142.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In acetonitrile; at 50 - 55℃; for 16h; | General procedure: A solution of benzimidazole 1a-c (1.0 mmol) in dry acetonitrile (0.3 ml) was added to a solution of phenylcyanoacetylene (2) (127 mg, 1.0 mmol) and isothiocyanate 3a-c (1.0 mmol) in dry acetonitrile (0.2 ml). The reaction mixture was stirred at 50-55C for 12-20 h. The solvent was removed, and carbothioamides 4a-e were separated by chromatography on an alumina column using 20:4:1 chloroform-benzene-ethanol as the eluent. N-[(Z)-2-Cyano-1-phenylethenyl]-N,1-dimethyl-1H-1,3-benzimidazole-2-carbothioamide (4a). Yield 199 mg, yellow powder, mp 166-167 (EtOH). IR spectrum, nu, cm-1: 2217 (C?N), 1611 (C=C), 1330 (C=S). 1H NMR spectrum, , ppm: 3.66 (3H, s, 9-CH3); 3.93 (3H, s, 1-CH3); 5.28 (1H, s, H-11); 7.15-7.55 (9H, m, H-4,5,6,7, H Ph). 13C NMR spectrum, , ppm: 32.6 (1-CH3); 42.6 (9-CH3); 91.6 (-11); 110.1 (-7); 115.6 (C-12); 121.0 (-5); 123.0 (-6); 124.1 (-o Ph); 128.3 (-4); 129.0 (-m Ph); 131.8 (-p Ph); 133.8 (-3);136.5 (-i Ph); 141.3 (-7); 149.1 (-2); 163.6 (-10); 190.1 (-8). Found, %: C 68.30; H 4.90; N 16.89; S 9.76. C19H16N4S. Calculated, %: C 68.65; H 4.85; N 16.85; S 9.64. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In acetonitrile; at 50 - 55℃; for 20h; | General procedure: A solution of benzimidazole 1a-c (1.0 mmol) in dry acetonitrile (0.3 ml) was added to a solution of phenylcyanoacetylene (2) (127 mg, 1.0 mmol) and isothiocyanate 3a-c (1.0 mmol) in dry acetonitrile (0.2 ml). The reaction mixture was stirred at 50-55C for 12-20 h. The solvent was removed, and carbothioamides 4a-e were separated by chromatography on an alumina column using 20:4:1 chloroform-benzene-ethanol as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With palladium 10% on activated carbon; triethylamine; at 150℃; for 0.133333h;Microwave irradiation; | The 0.152g (1.0mmol) <strong>[612-28-2]N-methyl-2-nitroaniline</strong> is dissolved in 0.8gTEAF (4.0mmol, 4 . 0equiv), and add 5.5mg10% Pd/C (0.5mol %). Suspension in the microwave heated to 150 C and lasts for 5 minutes. The reaction with TLC monitoring. The reaction mixture is added in 15 ml methanol and infusorial earth filtering to remove the catalyst. Removing the spin vaporization of methanol and add 10 ml saturated aqueous solution of sodium bicarbonate. After the gas of the escape, the reaction solution with 15 ml ethyl acetate extraction three times, and combined with the organic layer is dried with sodium sulfate. Removing the spin vaporization of the product of the ethyl ester of acetic acid 0.130g, the yield is 98%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With zinc(II) acetate dihydrate; In neat (no solvent); at 120℃; under 7600.51 Torr; for 18h;Autoclave; Inert atmosphere; Green chemistry; | General procedure: Zn(OAc)2·2H2O (5.0 mol%) was transferred to a 100 mL autoclavereactor equipped with an overhead stirrer and an automatic temperature-control system. The appropriate benzene-1,2-diamine 1 (2 mmol), DMF (10.0 mmol), and PMHS (5.0 mmol)were successively introduced. The reactor was sealed, flushedthree times with N2 (10 atm), and heated to the required temperature with vigorous stirring (600 rpm). During the course ofthe reaction, an increase of pressure was observed, due to thegeneration of Me2NH and HCHO at 120 C.15 (For this reason, the protocol needs to be performed in a sealed high-pressurereactor.) When the reaction was complete, the autoclave wascooled to r.t., and the pressure generated during the reactionwas carefully released. Basic hydrolysis was then carried out atr.t. for 30 min to remove unreacted PMHS from the mixture.13aThe mixture was then extracted with EtOAc (3 × 20 mL). Thecombined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude products were further purified bycolumn chromatography [silica gel (100-200 mesh), PE-EtOAc(20:4 to 10:2)]. The spectroscopic data for the products wereconsistent with those reported in the literature. |
31% | With phenylsilane; at 120℃; for 12h; | General procedure: A mixture of 1a (1b-1n, 0.4 mmol) and PhSiH3 (98 mL, 1.6 mmol)in N,N-dimethylformamide 2a (2b-2c, 1 mL) was stirred at 120 C for 12 h. When the reaction was completed, the resulting mixture was extracted with ethyl acetate three times. The combined organic layer was washed by NaCl aqueous solution and dried over anhydrous Na2SO4, after which the solvent was removed under reduced pressure. The residue was purified by column chromatography onsilica gel with petroleum ether and ethyl acetate (6:1-1:2) to give the corresponding product 3a (3b-3p). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 71% 2: 18% | With C8H7NO3; copper(ll) bromide In methanol at 45℃; for 24h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | for 3h;Inert atmosphere; Reflux; | 15 g (26.4 mmol) of compound 7 produced in Example 1-1 was placed in a 300-mL three-neck flask under nitrogen atmosphere, and 4-methyl-2-pentanone (150 mL) and 7.1 g (53.7 mmol) of 1-methylbenzimidazole were added thereto, followed by reflux under heating for 3 hours. After being allowed to cool down, the oily precipitate was washed with 4-methyl-2-pentanone (50 mL×2) and concentrated under reduced pressure to obtain 18.1 g (21.8 mmol, yield: 82%) of compound 14. 1H-NMR (500 MHz, Deuterated DMSO): delta=9.74 (s, 2H), 8.04 (m, 2H), 7.98 (m, 2H), 7.69 (m, 4H), 7.48 (d, J=8.5 Hz, 4H), 7.32 (d, J=8.5 Hz, 2H), 7.09 (d, J=8.5 Hz, 4H), 7.07 (d, J=8.5 Hz, H), 4.78 (t, J=6.0 Hz, 4H), 4.06 (s, 6H), 3.89 (t, J=6.0 Hz, 4H), 2.27 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In the reaction flask, Under argon, a catalyst (9.9 mg, 0.025 mmol, 5 mol%), potassium tert-butoxide (0.0672 g, 0.6 mmol) DMF (3.0 ml), 1-methylbenzimidazole (60.0 mul, 0.5 mmol) was added to the carbon dioxide gas, and the reaction was stirred at 80 C for 24 hours under normal pressure. Cooled to 65 C, methyl iodide (93 mul, 1.5 mmol) was added, The reaction was stirred at 65 C for 1 hour. Cooled to room temperature, the reaction was terminated with deionized water, The reaction product was extracted with ethyl acetate and purified by column chromatography (Using a mixed solvent of ethyl acetate / petroleum ether in a volume ratio of 1:10 as a developing solvent) The yield was 50%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.67 g | at 90℃; for 4h; | A mixture of 1-methylbenzimidazole (0.5 g, 3.75 mmol) and 2-chloroethylmethylether (0.35 g, 3.75 mmol) is heated at 90 C for 4 days without any solvent in 100 ml round bottom flask. After 4 days of stirring, white precipitated is isolated and washed with ethylacetate (twice with 25 mL) and dried in high vacuum. The so obtained white salt (0.67 g) is taken in methanol (50 mL) and treated with elemental sulphur (0.180 g, 5.63 mmol), anhydrouspotassium carbonate (0.780 g, 5.63 mmol). The reaction mixture is allowed to reflux for 20 h. The solution is then filtered in hot condition through celite. Filtrate is evaporated under reduced pressure to yield yellow crude which is purified by column chromatography packed with silica ethylacetate/hexane as mobile phase (50 % EAI Hexane). The desired product 1 -(2-methoxyethyl)-3-methyl-1 H-benzo[d]imidazole-2(3H)-thione (GP1 55) is obtained as awhite crystalline solid. Yield: 0.5 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 1-Methylbenzimidazole With trifluoroacetic acid In 1,2-dichloro-ethane at 20℃; for 0.166667h; Green chemistry; Stage #2: cyclohexylboronic acid With oxygen In 1,2-dichloro-ethane at 110℃; for 12h; Green chemistry; Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | A mixture of 2-chloropyridmiine (500 mg, 4.36 mmol) and 1-methylbenzimidazole (576.5 mg, 4.36 mmol) were heated neat at120 C with stirring for 20 h. 10 ml deionized was added to thechloride salt and a saturated aqueous solution (15 ml) of NH4PF6and was added and stirred at r.t. for 0.5 h. The white powderformed was filtered, dried in air, then recrystallized from CH3CN- diethyl ether, the yield was 1.39 g, 90%.1H NMR (CD3CN, 25 C), d = 4.01 (s, 3H, CH3), 7.74(t, J = 5.1 Hz,1H, p-H, pym.), 7.50-8.10 (m, 4H Ar-H), 8.95 (d, J = 4.9 Hz, 2H, m-H), 10.21 (s, 1H, NCHN), 13C NMR (400 MHz, CD3CN, 25 C) d =155.4 (m-C, pym), 154.9(i-C, pym), 139.9(NCN), 130.0, 129.4,118.5, 116.7, 115.9, 115.2 (Ar-C), 118.6 (p-C, pym), 36.8 (NACH3).Anal. Calc. for C12H11N4PF6: C, 40.45%; H, 3.08%; N, 15.73%; Found:C, 40.47%; H, 3.01%; N 15.71%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48.3 g | In a three-necked flask equipped with a water separator, a thermometer, a condenser, and a stirring device, 30 g of refined waste oil was added.39 g of N-methyl o-phenylenediamine and 70 ml of xylene were passed through nitrogen and slowly heated at 140 C. for 6.5 h. After evacuation at 190-200 mmHg, vacuum distillation was performed for 2.5-3 h and then at 20-25 mmHg. Distillation for 1 ~ 2h, until no liquid flow out, after cooling, add 110ml of 10% NaCl aqueous solution to the mixture and stir, heat the mixture to 80 C and heat 1h, cooled, let stand 2.0h, separated with a separatory funnel The upper oily substance was washed twice with water and the aqueous layer was separated. The oily phase was dried under vacuum to obtain a creamy oily fat-based inhibitor of N-methylbenzimidazoline, weighing 48.3 g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In N,N-dimethyl-formamide; at 70 - 110℃; for 26h;Inert atmosphere; Schlenk technique; | A mixture of 1-methylbenzimidazole (106?mg, 8?mmol) and <strong>[14140-15-9]4-(2-bromoethyl)phenol</strong> (161?mg, 8?mmol) was added in DMF (4?mL). The reaction mixture was stirred for 24?h?at 70-80?C and 2?h at 100-110?C temperature. Then the solvents were evaporated under vacuum to afford a white solid product. The crude product was recrystallized from ethyl alcohol/diethyl ether (1:3) at room temperature. Yield: 91% (242?mg), m.p.: 212-213?C; nu(CN): 1567?cm-1. 1H NMR (400?MHz, DMSO-d6), delta; 3.11 (t, 2H, -C6H4(OH)CH2CH2N-, J: 10.0?Hz); 4.07 (s, 3H, -NCH3); 4.69 (t, 2H, -C6H4(OH)CH2CH2N-, J: 10.0?Hz); 6.66 and 7.02 (d, 4H, -C6H4(OH), J: 12.0?Hz and 8.0?Hz Ar-H); 7.65-8.03 (m, 4H, Ar-H); 9.32 (s, 1H, -C6H4OH); 9.71 (s, 1H, 2-CH). 13C NMR (100?MHz, DMSO-d6) delta; 33.2 (-NCH3); 33.9 (-C6H4(OH)CH2CH2N-); 48.0 (-C6H4(OH)CH2CH2N-); 113.5, 113.6, 115.3, 126.4, 126.8, 129.7, 130.9, 131.6, 142.5, 131.4, 131.5, 132.2, 134.3, 134.9 and 138.8 (-C6H4(OH) and Ar-C); 156.2 (C-OH); 142.5 (2-CH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In N,N-dimethyl-formamide; at 70 - 110℃; for 26h;Inert atmosphere; Schlenk technique; | A mixture of 1-methylbenzimidazole (106?g, 8?mmol) and 1-(2-bromoethyl)-4-nitrobenzene (184?mg. 8?mmol) was added in DMF (4?mL). The reaction mixture was stirred for 24?h?at 70-80?C and 2?h at 100-110?C temperature. Then the solvents were evaporated under vacuum to afford the product as a white solid. The crude product was recrystallized from ethyl alcohol/diethyl ether (1:3) at room temperature. Yield: 229?g; (79%); m.p.: 144-145?C; nu(CN): 1568?cm-1. 1H NMR (400?MHz, DMSO-d6), delta; (t, 2H, -C6H4(NO2)CH2CH2N-, J: 7.2?Hz); 4.09 (s, 3H, -NCH3); 4.86 (t, 2H, -C6H4(NO2)CH2CH2N-, J: 6.0?Hz); 7.60-8.17 (m, 8H, Ar-H); 9.83 (s, 1H, 2-CH). 13C NMR (100?MHz, DMSO-d6) delta; 33.8 (-NCH3); 34.9 (-C6H4(NO2)CH2CH2N-); 47.4 (-C6H4(NO2)CH2CH2N-); 45.5 (-C6H4(NO2), Ar-C); 114.1, 124.1, 127.0, 130.9 and 143.3 (Ar-C); 1147.1 (C-NO2); 145.7 (2-CH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With ammonium peroxydisulfate; caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation; Green chemistry; regioselective reaction; | Procedure A for compounds (3a-3p) in Schemes 2 General procedure: Heterocycle (0.10mmol,1equiv)ammonium persulfate (0.30 mmol, 3 equiv), Cs2CO3(0.20mmol,2 equiv)were placed in a dry glass tube.Then, anhydrous DMSO1 mL) and2,2-diethoxyacetic acid (0.7mmol7equiv), wereinjected into the tube by syringe under a N2atmosphere.The solution was then stirred at roomtemperature under the irradiation of 15W blueLEDs strip for 24h.After completion of the reaction,the mixture was quenched by addition of1.2mL of 3.0 M HCl, stirred for 20hthen saturated Na2CO3solution was added to adjust pH tobasicextract with CH2Cl2,the combined organic layers was washed with brine, then dry overanhydrous Na2SO4. The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum and ethylacetate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With copper(l) iodide; palladium diacetate; In N,N-dimethyl-formamide; at 20 - 140℃; for 1h;Inert atmosphere; Sealed tube; Microwave irradiation; | General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With copper(l) iodide; palladium diacetate; In N,N-dimethyl-formamide; at 20 - 140℃; for 1h;Inert atmosphere; Sealed tube; Microwave irradiation; | General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With copper(l) iodide; palladium diacetate; In N,N-dimethyl-formamide; at 20 - 140℃; for 1h;Inert atmosphere; Sealed tube; Microwave irradiation; | General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(l) iodide; palladium diacetate; In N,N-dimethyl-formamide; at 20 - 140℃; for 1h;Inert atmosphere; Sealed tube; Microwave irradiation; | General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With ortho-tolylmagnesium bromide; bis(1,5-cyclooctadiene)nickel (0); C23H30N4 In m-xylene at 90℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With ortho-tolylmagnesium bromide; bis(1,5-cyclooctadiene)nickel (0); lithium chloride; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In m-xylene at 90℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With ortho-tolylmagnesium bromide; bis(1,5-cyclooctadiene)nickel (0); lithium chloride; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In m-xylene at 90℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | In dichloromethane; at 20℃;Inert atmosphere; | General procedure: The respective bromomethyl thiophene and imidazole were mixed in 10mL of methylene chloride to give a solution. The solution was stirred overnight at room temperature under an inert atmosphere. The solvent was removed under vacuum, resulting in a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; nixantphos In N,N-dimethyl-formamide at 70℃; for 24h; Glovebox; Inert atmosphere; | 2. A typical procedure for the Pd-catalyzed alkenylation of azole heterocycles General procedure: An oven-dried 10 mL reaction vial equipped with a stir bar was charged with azole heterocycles (1, 0.2 mmol, 1.0 equiv) and alkenyl bromides (2, 0.30 mmol, 1.5 equiv) in a glove box under a nitrogen atmosphere. A solution of catalytic Pd2(dba)3 (9.15 mg, 0.01 mmol, 5 mol%) and NiXantphos (11.03 mg, 0.02 mmol, 10 mol%) was stirred in 1 mL of dry tetrahydrofuran (THF) for 2 h at room temperature. Then, t-BuONa (57.7 mg, 0.6 mmol, 3.0 equiv) and reagent mixed with catalyst were added to the reaction mixture. And thenthe vial was capped. According to the temperature requirements for different products, some vials were stirred in the glove box for 24 h, but others were removed from the glove box, and stirred for 24 h at 70 or 150 . The reaction mixture was quenched with three drops of H2O, diluted with 3 mL of ethyl acetate, and filtered over a pad of silica. The pad was rinsed with ethyl acetate (15-25 mL), and the combined solutions were concentrated in vacuo. The crude material was loaded onto a deactivated silica gel column and purified by flash chromatography to afford the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sulfur; sodium dithionite; In 1,2-dichloro-ethane; at 120℃; for 24h;Sealed tube; | Add 1-methylbenzimidazole (0.4 mmol) to an oven-dried 15 mL sealed tube equipped with a magnetic stir bar with a magnetic stir bar,Sulfur powder (S8) (0.8 mmol), benzyl bromide (1.0 mmol),Under Na2S2O4 (0.8 mmol) as a catalyst,The solvent is 1,2-dichloroethane (DCE) (2.0 mL)The reaction in the solution was stirred at 80 C for 24 hours. After the reaction,The reaction mixture was cooled to room temperature and the mixture was extracted with dichloromethane.The combined organic layers were dried over anhydrous Na2SO4. Fast column chromatography using 300-400 mesh silica gel,Purification of the crude mixture (pure (PE): ethyl acetate (EA) = 6:1) by preparative TLC.M.p.: 134.0 to 135.0 C, yield 32. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With ammonium acetate; water at 140℃; for 10h; Inert atmosphere; Schlenk technique; | |
67% | With ammonium acetate In water at 140℃; for 11h; Schlenk technique; Inert atmosphere; | 13 In the dry Schlenk reaction tube, add N-methyl o-phenylenediamine (0.2 mmol), dimethyl sulfoxide (2 mL), ammonium acetate (1.2 mmol), and water (80 ul) in sequence. After the sample is added After evacuating with an oil pump, nitrogen was injected for gas replacement. After three replacements, the reaction was stopped at 140°C for 11 hours and then cooled to room temperature. The reaction is detected by thin layer chromatography (TLC). After the reaction of the raw materials is completed, the reaction is terminated, and the mixture in the reaction tube is cooled to room temperature. Preliminary treatment of the mixed solution: extraction, collecting the organic layer, spinning powder, and performing column chromatography to obtain the target product with a yield of 67%. |
Tags: 1632-83-3 synthesis path| 1632-83-3 SDS| 1632-83-3 COA| 1632-83-3 purity| 1632-83-3 application| 1632-83-3 NMR| 1632-83-3 COA| 1632-83-3 structure
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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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