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[ CAS No. 1221342-55-7 ] {[proInfo.proName]}

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Chemical Structure| 1221342-55-7
Chemical Structure| 1221342-55-7
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Product Details of [ 1221342-55-7 ]

CAS No. :1221342-55-7 MDL No. :MFCD14707563
Formula : C10H12N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 224.21 Pubchem ID :-
Synonyms :

Safety of [ 1221342-55-7 ]

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Application In Synthesis of [ 1221342-55-7 ]

* 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 [ 1221342-55-7 ]

[ 1221342-55-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 3113-71-1 ]
  • [ 6638-79-5 ]
  • [ 1221342-55-7 ]
YieldReaction ConditionsOperation in experiment
62% With carbon tetrabromide; triethylamine; triphenylphosphine In dichloromethane for 2.5h; Inert atmosphere;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; 40.a N-Methoxy-N,3-dimethyl-4-nitrobenzamide Triethylamine (7.6 mL, 54.651 mmol) was added slowly to a mixture of 3-methyl-4-nitrobenzoic acid (5 g, 27.326 mmol), N,O-dimethylhydroxylamine hydrochloride (2.99 g, 30.058 mmol), and EDCI (6.28 g, 32.791 mmol) in DCM (30 mL). The mixture was stirred at room temperature overnight, quenched with saturated aqueous NaHCO3 and stirred at room temperature for 30 minutes. Water (50 mL) was added followed by additional DCM. The mixture was stirred for 10 minutes and layers were separated. The aqueous layer was again extracted with DCM. The combined organic layer was dried over Na2SO4, then filtered. The solvent was removed and the residual oil chromatographed (DCM/EtOAc) to provide the product as a white solid.
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water at 20℃; for 0.5h; 13.a N-Methoxy-N,3-dimethyl-4-nitrobenzamide Triethylamine (7.6 mL, 54.65 mmol) was added slowly to a mixture of 3-methyl-4-nitrobenzoic acid (5 g, 27.33 mmol), N,O-dimethylhydroxylamine hydrochloride (2.99 g, 30.06 mmol), and EDCI (6.28 g, 32.79 mmol) in DCM (30 mL). The mixture was stirred at room temperature overnight, quenched with saturated aqueous NaHCO3 and stirred at room temperature for 30 minutes. Water (50 mL) was added followed by additional DCM. The mixture was stirred for 10 minutes and layers were separated. The aqueous layer was again extracted with DCM. The combined organic layer was dried over Na2SO4, then filtered. The solvent was removed and the residual oil chromatographed (DCM/EtOAc) to provide the title compound as a white solid.
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; 13a Intermediate 13: step a
N-methoxy-N,3-dimethyl-4-nitrobenzamide Intermediate 13: step aN-methoxy-N,3-dimethyl-4-nitrobenzamideTriethylamine (7.6 mL, 54.65 mmol) was added slowly to a mixture of 3-methyl-4-nitrobenzoic acid (5 g, 27.33 mmol), N,O-dimethylhydroxylamine hydrochloride (2.99 g, 30.06 mmol), and EDCI (6,28 g, 32.79 mmol) in DCM (30 mL). The mixture was stirred at room temperature overnight, quenched with saturated aqueous NaHCO3 and stirred at room temperature for 30 minutes. Water (50 mL) was added followed by additional DCM. The mixture was stirred for 10 minutes and layers were separated. The aqueous layer was again extracted with DCM, The combined organic layer was dried over Na2SO4, then filtered. The solvent was removed and the residual oil chromatographed (DCM/EtOAc) to provide the title compound as a white solid.
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; 14.a N-Methoxy-N,3-dimethyl-4-nitrobenzamide Triethylamine (37.9 mL, 273 mmol) was added slowly to a mixture of 3-methyl-4-nitrobenzoic acid (25.0 g, 136 mmol), N,O-dimethylhydroxylamine hydrochloride (14.95 g, 150.3 mmol), and EDCI (31.40 g, 163.9 mmol) in DCM (171 mL). The mixture was stirred at room temperature overnight, quenched with saturated aqueous NaHCO3 and stirred at room temperature for 30 minutes. Water (50 mL) was added followed by additional DCM. The mixture was stirred for 10 minutes and layers were separated. The aqueous layer was again extracted with DCM. The combined organic layers were dried over MgSO4, then filtered. The solvent was removed and the residual oil chromatographed (0 to 20% EtOAc/DCM) to provide the title compound as a yellow oil.
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; 14.a Intermediate 14:
step a
N-methoxy-N,3-dimethyl-4-nitrobenzamide
Intermediate 14: step a N-methoxy-N,3-dimethyl-4-nitrobenzamide Triethylamine (37.9 mL, 273 mmol) was added slowly to a mixture of 3-methyl-4-nitrohenzoic acid (25.0 g, 136 mmol), N,0-dimethylhydrox lamine hydrochloride (54.95 g, 150.3 mmol), and EDCI (31.40 g, 163.9 mmol) in DCM (571 mL), The mixture was stirred at room temperature overnight, quenched with saturated aqueous NaHC03and stirred at room temperature for 30 minutes. Water (50 mL) was added followed by additional DCM. The mixture was stirred for 50 minutes and layers were separated. The aqueous layer was again extracted with DCM. The combined organic layers were dried over MgS04, then filtered. The solvent was removed and the residual oil chromatographed (0 to 20% EtOAe/DCM) to provide the title compound as a yellow oil.
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; 13.a N-methoxy-N,3-dimethyl-4-nitrobenzamide Triethylamine (7.6 mL, 54.65 mmol) and DCM (30 mL) of 3-methyl-4-nitrobenzoic acid (5 g, 27.33 mmol),N,O-dimethylhydroxylaminehydrochloride (2.99 g, 30.06 mmol ) and EDCI (6.28 g, was slowly added to a mixture of 32.79 mmol).The mixture was stirred overnight at room temperature, saturated NaHCO3quenched with an aqueous solution, was stirred for 30 minutes at room temperature.Water (50 mL), was added followed by additional DCM.The mixture was stirred for 10 minutes, the layers were separated.The aqueous layer was re-extracted with DCM.The combined organic layer is Na2SO4in the following by drying, and filtered.The solvent was removed, the remaining oil was analyzed by chromatography (DCM / EtOAc), to give the title compound as a white solid.

  • 2
  • [ 1003-21-0 ]
  • [ 1221342-55-7 ]
  • [ 1599529-32-4 ]
YieldReaction ConditionsOperation in experiment
A solution of EtMgBr (3.0 M in diethylether, 8.5 mL, 25.689 mmol) was added dropwise, over a 25 minutes period, to a solution of <strong>[1003-21-0]5-bromo-1-methyl-1H-imidazole</strong> (4.1 g, 25.689 mmol) in dry DCM (25 mL). The mixture was stirred at room temperature for 15 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (4.8 g, 21.408 mmol, Intermediate 40: step a) dissolved in 10 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and mixture stirred at room temperature for 48 hours. Water was added to the suspension followed by 6M aqueous HCl slowly to neutralize the mixture (pH=6-7). More DCM was added and layers separated. The organic layer was dried over Na2SO4, filtered and concentrated. Et2O was added, the slurry sonicated, and precipitates filtered to provide the title compound as a tan solid.
A solution of EtMgBr (3.0 M in diethylether, 8.5 mL, 25.69 mmol) was added dropwise, over a 25 minute period to a solution of <strong>[1003-21-0]5-bromo-1-methyl-1H-imidazole</strong> (4.1 g, 25.69 mmol) in dry DCM (25 mL). The mixture was stirred at room temperature for 15 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (4.8 g, 21.41 mmol. Intermediate 13: step a) dissolved in 10 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and the mixture stirred at room temperature for 48 hours. Water was added to the suspension followed by 6 M aqueous HCl slowly to neutralize the mixture (pH=6-7). More DCM was added and the layers were separated. The organic layer was dried over Na2SO4, filtered and concentrated. Et2O was added, the slurry sonicated, and the precipitates filtered to provide the title compound as a tan solid.
Intermediate 13: step b(1-Methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanoneA solution of EtMgBr (3.0 M in diethylether, 8.5 mL, 25.69 mmol) was added dropwise, over a 25 minute period to a solution of <strong>[1003-21-0]5-bromo-1-methyl-1H-imidazole</strong> (4.1 g, 25.69 mmol) in dry DCM (25 mL). The mixture was stirred at room temperature for 15 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (4.8 g, 21.41 mmol, Intermediate 13: step a) dissolved in 10 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and the mixture stirred at room temperature for 48 hours. Water was added to the suspension followed by 6 M aqueous HCl slowly to neutralize the mixture (pH = 6-7). More DCM was added and the layers were separated. The organic layer was dried over Na2SO4, filtered and concentrated. Et2O was added, the slurry sonicated, and the precipitates filtered to provide the title compound as a tan solid.
A solution of EtMgBr (3.0 M in diethylether, 15.1 mL, 45.2 mmol) was added dropwise, to a solution of <strong>[1003-21-0]5-bromo-1-methyl-1H-imidazole</strong> (7.28 g, 45.2 mmol) in dry DCM (40 mL) at 0 C. and stirred for 10 minutes. The mixture was then stirred at room temperature for 30 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (8.45 g, 37.7 mmol, Intermediate 14: step a) dissolved in 22 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and mixture stirred at room temperature for 18 hours. Water was added to the suspension followed by 6 M aqueous HCl slowly to neutralize the mixture (pH=6-7). More DCM was added and layers separated. The organic layer was dried over MgSO4, filtered and concentrated. Et2O was added, the slurry sonicated, and precipitates were filtered and dried to provide the title compound.
Intermediate 14: step b (1-methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone A solution of EtMgBr (3.0 M in diethylether, 15.1 niL, 45.2 mmol) was added dropwise, to a solution of 5-bromo-l -methyl- 1H- imidazole (7.28 g, 45.2 mmol) in dry DCM (40 ml.) at 0 C and stirred for 10 minutes. The mixture was then stirred at room temperature for 30 minutes, cooled in an ice-brine bath and N-methoxy-N,3-dimethyl-4-nitrobenzamide (8.45 g, 37.7 mmol, Intermediate 14: step a) dissolved in 22 mL of DCM was added dropwise. A dark brown solid mass formed. The ice bath was removed and mixture stirred at room temperature for 18 hours. Water was added to the suspension followed by 6 M aqueous HC1 slowly to neutralize the mixture (pH = 6-7). More DCM was added and layers separated. The organic layer was dried over MgSC>4, filtered and concentrated. Et20 was added, the slurry sonicated, and precipitates were filtered and dried to provide the title compound.
EtMgBr solution (diethyl ether in 3.0 M, 8.5 mL, 25.69 mmol) and dry DCM (25 mL) of 5-bromo-1-methyl -1H-imidazole(4.1 g, 25.69 mmol) in solution in 25 bungan It was added dropwise over.The mixture is stirred at room temperature for 15 minutes, ice-cooled in the brine bath, dissolved in DCM 10 mLN-methoxy-N, 3- dimethyl-4-nitrobenzamide (4.8 g, 21.41 mmol, Intermediate 13: It was added dropwise to step a).Dark brown solids were produced.The ice bath was removed and the mixture was stirred at room temperature for 48 hours.After water was added to the suspension by the addition of 6M HCl aqueous solution slowly, and the mixture was neutralized (pH = 6-7).By the addition of further DCM, the layers were separated.The organic layer is Na2SO4dried and, filtrated, and concentrated.Et2by the addition of O, the sonicated slurry and the precipitate was filtered to give the title compound as a tan solid.

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