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Chemical Structure| 426219-43-4 Chemical Structure| 426219-43-4

Structure of 426219-43-4

Chemical Structure| 426219-43-4

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Product Details of [ 426219-43-4 ]

CAS No. :426219-43-4
Formula : C6H6N2O
M.W : 122.12
SMILES Code : O=C1CCN2C=NC=C12
MDL No. :MFCD17013182

Safety of [ 426219-43-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 426219-43-4 ]

* 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 [ 426219-43-4 ]

[ 426219-43-4 ] Synthesis Path-Downstream   1~3

  • 1
  • aqueous ammonium chloride [ No CAS ]
  • n-butyllithium hexane [ No CAS ]
  • [ 426219-35-4 ]
  • [ 426219-43-4 ]
  • [ 426219-18-3 ]
YieldReaction ConditionsOperation in experiment
With ammonia; In tetrahydrofuran; Example 5 Production of 6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide Dry THF (150 ml) was cooled to -65 C. in a dry ice-acetone bath under an argon atmosphere and n-butyl lithium hexane solution (1.6M: 45.2 ml) was added. A solution of <strong>[426219-35-4]6-bromo-N-methyl-2-naphthamide</strong> (8.68 g) in dry THF (700 ml) cooled to 10 C. was added to this solution at not more than -55 C., and the mixture was stirred for 1 h. A dry THF solution (60 ml) of 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (3.65 g) was added dropwise. The mixture was stirred at the same temperature for 1.5 h and saturated aqueous ammonium chloride solution (120 ml) was added to stop the reaction. The solvent was evaporated under reduced pressure and an ethanol-soluble material was extracted from the resulting residue and the solvent was evaporated again. The residue was purified by flash silica gel column chromatography (eluent, chloroform/methanol containing ammonia (7%), 19/1?9/1). The elude was recrystallized from methanol to give the title compound (3.36 g) as colorless crystals. 1H-NMR(CDCl3+CD3OD) delta: 2.89-3.02(2H, m), 3.04(3H, s), 4.124.25(1H, m), 4.27-4.43(1H, m), 6.79(1H, s), 7.20(1H, q, J=4.6 Hz), 7.54(1H, s), 7.63(1H, dd, J=1.8 Hz, 8.6 Hz), 7.83(2H, s), 7.89(1H, d, J=8.6 Hz), 8.03(1H, s), 8.28(1H, s). IR(KBr):3500-3000, 1644, 1605, 1559, 1497, 1464, 1318, 1082 cm-1.
  • 2
  • aqueous ammonium chloride [ No CAS ]
  • n-butyllithium hexane [ No CAS ]
  • [ 426219-35-4 ]
  • [ 392-83-6 ]
  • [ 426219-43-4 ]
  • [ 426219-18-3 ]
YieldReaction ConditionsOperation in experiment
With ammonia; In tetrahydrofuran; Example 10 Production of 6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide Under an argon atmosphere, 2-bromobenzotrifluoride (33.05 g) was dissolved in dry THF (600 ml), and the mixture was cooled to -65 C. in a dry ice-acetone bath. An n-butyl lithium hexane solution (1.6M: 93.7 ml) was added with stirring and the mixture was stirred at the same temperature for 30 min. After stirring the mixture, a dry THF (2.88L) solution of <strong>[426219-35-4]6-bromo-N-methyl-2-naphthamide</strong> (38.03 g) cooled to 10 C. was added at not more than -55 C. The mixture was stirred for 20 min. An n-butyl lithium hexane solution (1.6M: 94.5 ml) was added at not more than -65 C. The mixture was stirred for 30 min and 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (14.66 g) in a dry THF solution (240 ml) was added dropwise. The mixture was stirred at the same temperature for 1.5 h and saturated aqueous ammonium chloride solution (520 ml) was added to stop the reaction. The solvent was evaporated under reduced pressure and an ethanol-soluble material was extracted from the resulting residue and the solvent was evaporated again. The resulting residue was purified by flash silica gel column chromatography (eluent; chloroform/methanol containing ammonia (7%); 19/1?9/1). The elude was recrystallized from methanol to give the title compound (16.44 g) as colorless crystals. The physical and chemical data were identical with those of the compound obtained in Example 5.
  • 3
  • [ 426219-35-4 ]
  • [ 426219-43-4 ]
  • [ 426219-18-3 ]
YieldReaction ConditionsOperation in experiment
45% Under an argon atmosphere, 2-bromobenzotrifluoride (33.05 g, 147 mmol) was dissolved in dry THF (600 mL) and the mixture was cooled to -65 C in a dry ice acetone bath. A n-BuLi hexane solution (1.6 M: 93.7 mL, 150 mmol) was added with stirring and the mixture was stirred at the same temperature for 30 min. After stirring, a cooled (10 C) solution of 9a (38.03 g, 144 mmol) in dry THF (2.88 L) was added at not more than -55 C and the mixture was stirred for 20 min. An additional n-BuLi hexane solution (1.6 M: 94.5 mL, 151 mmol) was added at not more than -65 C and the mixture was further stirred for 30 min. To the mixture, a solution of 6 (14.66 g, 120 mmol) in a dry THF solution (240 mL) was added dropwise and the resulting solution was stirred at the same temperature for 1.5 h. After dilution with saturated aqueous ammonium chloride solution, the mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethanol and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure and the resulting residue was chromatographed on silica gel (CHCl3/7% ammonia in MeOH = 19:1 to 9:1) and recrystallized from MeOH to give 3c (16.44 g, 45%) as a colorless powder. The spectral data were identical to those of the authentic sample.
 

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