1,4-Bis(imidazole-l-ylmethyl)benzene synthesis
- Product Name:1,4-Bis(imidazole-l-ylmethyl)benzene
- CAS Number:56643-83-5
- Molecular formula:C14H14N4
- Molecular Weight:238.29
288-32-4
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Yield: 100%
Reaction Conditions:
Stage #1:1H-imidazole with sodium hydride in tetrahydrofuran;mineral oil at 0 - 20; for 2 h;Inert atmosphere;
Stage #2:1,4-bis(bromomethyl)benzene in tetrahydrofuran;mineral oil for 6 h;Reflux;Inert atmosphere;
Steps:
3.2. Synthesis of NHC Precursors
General procedure: Synthesis of 9 and 12. Sodium hydride (60% in oil, 2.2 g, 55.0 mmol) was slowly added toimidazole (7, 3.5 g, 51.4 mmol) or benzimidazole (11, 6.0 g, 50.8 mmol) in dry THF (150 mL) at 0 C,and the resulting suspension was stirred at rt for 2 h (until the hydrogen gas evolution ceased). Then 8(for 9, 13.2 g, 50.0 mmol) or 10 (for 12, 10.1 g, 50 mmol) was added, and the resulting mixture wasrefluxed for 6 h more. The solvent was then removed under vacuum and the thus obtained crudeproduct was dissolved in dichloromethane (150 mL) and washed with water (100 mL). The aqueousphase was extracted with dichloromethane (2 150 mL). The combined organic layers were washedwith a saturated NaCl solution (200 mL), dried over anhydrous magnesium sulfate and filtered.After removal of the solvent under reduced pressure, the product was redissolved in dichloromethane(15 mL) and slowly added dropwise into diethyl ether (350 mL) to precipitate the pure product. The product 9 or 12 was dried at 70 C under vacuum overnight and obtained in quantitative yield.See Supplementary Materials for NMR spectra. 1,1'-(p-Phenylenedimethylene)bisimidazole (9). White solid. 1H-NMR (400 MHz, CDCl3, ppm): 5.11(s, 4H), 6.88 (s, 2H), 7.09 (s, 2H), 7.13 (s, 4H), 7.53 (s, 2H). 13C-NMR (100 MHz, CDCl3): 50.4, 119.3,127.9, 130.1, 136.5, 137.5. LRMS for C14H14N4: calcd 238.1, found 238.0.
References:
Ma, Shuang;Toy, Patrick H. [Molecules,2016,vol. 21,# 8,art. no. 1100]
288-32-4
964 suppliers
$5.00/25g
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56643-83-5
79 suppliers
$60.00/100mg
288-32-4
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104-81-4
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56643-83-5
79 suppliers
$60.00/100mg