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Chemical Structure| 958245-17-5 Chemical Structure| 958245-17-5

Structure of 958245-17-5

Chemical Structure| 958245-17-5

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Product Details of [ 958245-17-5 ]

CAS No. :958245-17-5
Formula : C11H11N3O3
M.W : 233.22
SMILES Code : COC1=C(C=CC(=C1)[N+]([O-])=O)N1C=NC(C)=C1
MDL No. :MFCD11870474

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Application In Synthesis of [ 958245-17-5 ]

* 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 [ 958245-17-5 ]

[ 958245-17-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 822-36-6 ]
  • [ 454-16-0 ]
  • [ 958245-17-5 ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate; In dimethyl sulfoxide; at 125℃; for 16h;Autoclave; Inert atmosphere; 2-Fluoro-5-nitroanisole (50 g, 0.29 mol) was added to a solution of 4-methyl-lH- imidazole (36.0 g, 0.44 mol) and K2C03 (40.38 g, 0.29 mol) in DMSO (150 ml) in a stainless steel autoclave under a N2 atmosphere. The vessel was closed and the r.m. was heated at 125 °C for 16 h. Subsequently, the mixture was cooled and the solvent was evaporated under reduced pressure. H20 (q.s.) was added to the residue and the precipitated product was collected by filtration. This solid was then triturated with DIPE and collected by filtration to yield a light-brown solid. Yield: 53.8 g of intermediate 40(79 percent).
79% With potassium carbonate; In dimethyl sulfoxide; at 125℃; for 16h;Inert atmosphere; 2-Fluoro-5-nitroanisole (50 g, 0.29 mol) was added to a solution of 4-methyl-lH- imidazole (36.0 g, 0.44 mol) and K2C03 (40.38 g, 0.29 mol) in DMSO (150 ml) in a stainless steel autoclave under a N2 atmosphere. The vessel was closed and the r.m. was heated at 125 °C for 16 h. Subsequently, the mixture was cooled and the solvent was evaporated under reduced pressure. H20 (q.s.) was added to the residue and the precipitated product was collected by filtration. This solid was then triturated with DIPE and collected by filtration to yield a light-brown solid. Yield: 53.8 g of intermediate 40 (79 percent).
79% With potassium carbonate; In dimethyl sulfoxide; at 125℃; for 16h;Inert atmosphere; 2-Fluoro-5-nitroanisole (50 g, 0.29 mol) was added to a solution of 4-methyl-1H-imidazole (36.0 g, 0.44 mol) and K2CO3 (40.38 g, 0.29 mol) in DMSO (150 ml) in a stainless steel autoclave under a N2 atmosphere. The vessel was closed and the r.m. was heated at 125° C. for 16 h. Subsequently, the mixture was cooled and the solvent was evaporated under reduced pressure. H2O (q.s.) was added to the residue and the precipitated product was collected by filtration. This solid was then triturated with DIPE and collected by filtration to yield a light-brown solid. Yield: 53.8 g of intermediate 40 (79percent).
78.9% With potassium carbonate; In dimethyl sulfoxide; at 125℃; for 16h;Inert atmosphere; Autoclave; Example A2 a) Preparation of intermediate 3. (NOTE: this reaction was carried out in 4 batches of 50 g of <strong>[454-16-0]2-fluoro-5-nitroanisole</strong>). A mixture of <strong>[454-16-0]2-fluoro-5-nitroanisole</strong> (200 g, 1.17 mol), 4-methyl- IH- imidazole (143.9 g, 1.75 mol) and K2CO3 (161.5 g, 1.17 mol) in DMSO (600 ml) was prepared in a stainless steel autoclave under a N2 atmosphere. The vessel was closed and the r.m. heated at 125 0C for 16 h. The contents were allowed to cool and the solvent was evaporated under reduced pressure. H2O (q.s.) was added to the residue and the precipitated product was collected by filtration. This solid was then triturated with DIPE and collected by filtration to yield a light-brown solid. Yield: 215 g ofintermediate 3 (78.9 percent).
With potassium carbonate; In acetonitrile; at 20℃; Step C:; Two equivalent of 4-methylimidazole, 1 equivalent of 3-methoxy-4-fluoro- nitrobenzene and 5 eq. of K2CO3 were stirred in CH3CN at room temperature over night. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was recrystalized with EtOAc to give desired product 5.1 d.
With potassium carbonate; In acetonitrile; at 20℃; Step F: Two equivalent of 4-methylimidazofe, 1 equivalent of 3-rnethoxy-4-fluoro- nitrobenzene and 5 eq. of K2CO3 were stirred in CH3CN at room temperature over night. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was recrystalized with EtOAc to give desired product E1i.
With potassium carbonate; In acetonitrile; at 20℃; 4-methylimidazole (2.0 mmol), <strong>[454-16-0]3-methoxy-4-fluoro-nitrobenzene</strong> (1.0 mmol) and K2CO3 (5 mmol) were stirred in CH3CN (10 mL) at room temperature over night. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was recrystallized with EtOAc to give desired product 1a.
With potassium carbonate; In acetonitrile; at 20℃; EXAMPLE 1Step A: 4-methylimidazole (2.0 mmol), <strong>[454-16-0]3-methoxy-4-fluoro-nitrobenzene</strong> (1.0 mmol) and K2CO3 (5 mmoi) were stirred in CH3CN (10 mL) at room temperature over night. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was recrystalized with EtOAc to give desired product 1a.
With potassium carbonate; In N,N-dimethyl-formamide; at 85℃;Sealed tube; Example 34 a. 3-methoxy-4-(5-methyl-lH-imidazol-l-yl)anilineA mixture of 4-methyl imidazole (500 mg, 6.1 mmol), 2-fluoro-5-nitro anisole (1.02 g, 5.9 mmol) and potassium carbonate (1.68 g, 12 mmol) in DMF (15 mL) was heated overnight at 85°C in a sealed tube. The reaction mixture was cooled, transferred into a round bottom flask using ethyl acetate and concentrated under high vacuum to 5 mL volume. The residue was suspended in water and extracted with dichloromethane. The organic extracts were combined, washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The residue was dissolved in dichloromethane (10 mL) and diluted with hexane until the solution became slightly turbid. The turbid solution was left at room temperature. The separated solid was filtered, washed with hexane to give l-(2-methoxy-4-nitro-phenyl)-4- methyl-lH-imidazole. The mother liquor was purified by preparative HPLC giving 0.20 g of l-(2-methoxy-4-nitro-phenyl)-5-methyl-lH-imidazole.10 percent Pd/C (0.28 g, 2.6 mmol) was added to a solution of l-(2-methoxy-4-nitro-phenyl)-5- methyl-lH-imidazole (0.61 g, 2.6 mmol) in ethyl acetate (20 mL). The mixture was hydrogenated at 35 psi over night. The mixture was filtrated through celite and concentrated to about 10 mL. Diethylether (50 mL) was added and the solution was cooled to 00C. 4M HCl in dioxane (2 mL) was added and the solution was stirred for 15 min then warmed up to rt and stirred for 30 min. The excess solvent was decanted off and more diethylether was added and the mixture stirred for 15 min. This was repeated once more with a large amount of diehtylether. The wet solid was dried under vacuum giving 0.60 g of the title compound (16 percent Yield).1H NMR (400 MHz, METHANOL-d4) ppm 2.15 (s, 3 H), 3.92 (s, 3 H), 7.07 (dd, 1 H), 7.19 (d, 1 H), 7.49 (s, 1 H), 7.59 (d, 1 H), 9.03 (d, 1 H)

  • 2
  • [ 822-36-6 ]
  • [ 454-16-0 ]
  • [ 958245-17-5 ]
  • [ 1255701-91-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 85℃; A mixture of 4-methyl imidazole (500 mg, 6 mmol), 2-fluoro-5-nitro anisole (1.02 g, 5.9 mmol) and potassium carbonate (1.68 g, 12 mmol) in DMF (15 mL) was heated overnight at 850C in a sealed tube. The reaction mixture was cooled, transferred into a round bottom flask using ethyl acetate and concentrated under high vacuum to 5 mL volume. The residue was suspended in water and extracted with dichloromethane (3 x 25 mL). The organic extracts were combined, washed with brine, dried over anhydrous MgSO4, filtered and concentrated to give an orange solid. The solid was dissolved in dichloromethane (10 mL) and diluted with hexane until the solution became slightly turbid. The turbid solution was left at room temperature. The separated orange solid was filtered, washed with hexane to give l-(2-methoxy-4-nitro-phenyl)-4-methyl-lH-imidazole and l-(2-methoxy-4-nitro- phenyl)-5 -methyl- lH-imidazole (577 mg, 43 percent).1H NMR (400 MHz, methanol- d4) delta ppm 2.25 (s, 3 H) 4.02 (s, 3 H) 7.21 (s, 1 H) 7.62 (d, 1 H) 7.92 - 8.02 (m, 2 H) 8.04 (s, 1 H)
 

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