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CAS No. : | 112362-30-8 | MDL No. : | MFCD23135291 |
Formula : | C21H17N5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 339.39 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H317-H319 | Packing Group: | |
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 |
---|---|---|
82% | Stage #1: 2,6-bis(benzimidazole-2'-yl)pyridine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 16h; | |
81% | Stage #1: 2,6-bis(benzimidazole-2'-yl)pyridine With sodium hydride In N,N-dimethyl-formamide at 35℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 40℃; for 3h; | 3.2 Under an atmospheric nitrogen gas flow, sodium hydride in an amount of 12.8 mmol (containing 438 mg of 30 % liquid paraffin) was placed into a three neck flask having a capacity of 100 milliliter, and adding n-pentane in an amount of 10 milliliter, the resultant solution was stirred at room temperature for 15 minutes. Subsequently, n-pentane was removed and then, after adding n-pentane again, the resultant solution was stirred. Repeating the above operation 4 times totally, the liquid paraffin was removed. Afterwards, the refined sodium hydride was vacuum dried among the flask. Thereafter, adding 10 milliliter of N, N-dimethylformamide and hbip in an amount of 3.2 mmol (1.0 g), the resultant solution was further stirred for 1 hour at a temperature of 35 °C. Further adding methyl iodide in an amount of 9.6 mmol (1.36 g), the resultant solution was stirred at a temperature of 40 °C for 3 hours. After the resultant solution was cooled by leaving it standing, 50 milliliter of pure water was added and a generated precipitate was collected by filtration followed by drying, and as a result, 0.87 g of the aimed substance was obtained (yield: 81 %). |
52% | Stage #1: 2,6-bis(benzimidazole-2'-yl)pyridine With potassium hydroxide In acetone at 20℃; for 0.25h; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: methyl iodide In acetone at 20℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox; |
46% | Stage #1: 2,6-bis(benzimidazole-2'-yl)pyridine With potassium hydroxide In acetone at 20℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In acetonitrile Inert atmosphere; | |
16% | Stage #1: 2,6-bis(benzimidazole-2'-yl)pyridine With sodium hydride; tetramethylurea at 0 - 35℃; for 1.5h; Stage #2: methyl iodide at 0 - 40℃; | Synthesis of Me2bimpy Me2bimpy was prepared using the procedures described inliterature. 1 Specifically, to a solution of Bimpy (100 mg, 0.3 mmol) in tetramethylurea (TMU, 0.6 mL) was added a mixture of NaH (60%, 39 mg, 1 mmol) in TMU (0.6 mL). The resulting mixture was stirred at 0 C for 0.5 h and then at 35 C for another 1 h. After the mixture was cooled to0 C, MeI (60 μL) was added and the reactionmixture was stirred overnight at 40 C. Water wasadded to quench the reaction and the resulting mixture was concentrated underreduced pressure. The obtained residue was purified by chromatography on asilica-gel column, eluted by a mixture of CH2Cl2 and CH3OH (20/1,v/v) to give Me2bimpy (17 mg, 16%) having 1H NMR (CD3OD,400 MHz) δ 8.35 (d, J= 8.0 Hz, 2H), 8.24 (dd, J = 7.6 Hz,1H), 7.78 (d, J = 7.6 Hz, 2H), 7.65 (d,J = 8.0 Hz, 2H), 7.43 (dd, J = 7.2 Hz, 2H), 7.38 (dd, J = 7.6 Hz, 2H), 4.28 (s, 6H) andESI-MS: m/z 363.06 ([M+Na]+). |
With sodium hydride 1.) tetramethylurea (TMU), 35 deg C, 1h, 2.) tetramethylurea, 40 deg C, 3 h; Yield given. Multistep reaction; | ||
With sodium hydride | ||
Stage #1: 2,6-bis(benzimidazole-2'-yl)pyridine With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 50℃; Inert atmosphere; | ||
463 mg | Stage #1: 2,6-bis(benzimidazole-2'-yl)pyridine With potassium hydroxide In acetone at 20℃; for 0.25h; Stage #2: methyl iodide In acetone at 20℃; for 16h; | |
With potassium hydroxide Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With polyphosphoric acid at 210℃; for 4h; Neat (no solvent); | |
90% | Stage #1: Pyridine-2,6-dicarboxylic acid; N-methyl-1,2-phenylenediamine With phosphoric acid In water at 250℃; for 24h; Inert atmosphere; Stage #2: With potassium hydroxide In water for 2h; Cooling with ice; | |
90% | With phosphoric acid In water at 250℃; for 24h; Inert atmosphere; |
85% | With phosphoric acid at 230℃; for 4h; | This ligand was prepared by a modification of the procedure reported for 2,6-bis(benzimidazol-2-yl)pyridine.4 A mixture of pyridine-2,6-dicarboxylic acid (3.35 g, 20 mmol) and N-methyl-1,2-phenylenediamine (5.38 g, 44 mmol) in 40 mL of 85% phosphoric acid was stirred at ca 230° C. for 4 h. The dark green melt was poured into 1 L of vigorously stirred cold water. After it was cooled to room temperature, the blue precipitate was collected by filtration, then slurried into 300 mL of hot aqueous sodium carbonate solution (10%). The resulting solid was filtered off and recrystallized from methanol to give a white solid. Yield: 5.77 g, 85%. NMR (CDCl3): δ 8.42 (d, 2H), 8.05 (t, 1H), 7.86-7.89 (m, 2H), 7.44-7.48 (m, 2H), 7.33-7.41 (m, 4H), 4.25 (s, 6H, 2CH3). This ligand was pure by 1H-NMR and was used without further purification |