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Chemical Structure| 51818-19-0 Chemical Structure| 51818-19-0

Structure of 51818-19-0

Chemical Structure| 51818-19-0

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Product Details of [ 51818-19-0 ]

CAS No. :51818-19-0
Formula : C8H10N2O
M.W : 150.18
SMILES Code : N=C(N)C1=CC=CC=C1OC
MDL No. :MFCD05663332

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Application In Synthesis of [ 51818-19-0 ]

* 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 [ 51818-19-0 ]

[ 51818-19-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 6609-56-9 ]
  • [ 51818-19-0 ]
YieldReaction ConditionsOperation in experiment
80 - 91% To anhydrous ether at O0C was introduced to flask under argon, LiHMDS (94 ml, 93.9 rηmol) was introduced and stirred for 5 min^<strong>[6609-56-9]2-methoxy-benzonitrile</strong> (5g, 37.6 mmol) was then added and the mixture was stirred at room temperature for 3 days. When all the starting material is consumed the reaction mixture was concentrated and 200 mL of cold 1 N HCI was added and stirred for 0.5 h. The aqueous layer was extracted with diethyl ether then adjusted the pH of the aqueous layer to 13 by addition of 6N NaOH. The 2-(methyloxy)benzenecarboxirnidamide free base was extracted with dichloromethane (x3). The combined organic layers were dried over Na2SO4 and concentrated to give pure product in 91% yield.; 2-Methoxybenzonitrile (5 g, 37.5 mmol) was added to a 0 0C solution of LiHMDS (94 ml_, 1M in hexanes) in anhydrous Et2O (75 mL, 0.5 M) under N2. After warming to room temperature, the mixture stirred for three days. The resulting reaction mixture was quenched by the addition of 1 N HCI. The layers were separated and the aqueous phase was extracted 2 times with Et2θ. The aqueous layer was cooled in an ice-bath, adjusted to pH 12, and extracted 3 times with dichlormethane. The organic portions were pooled, dried over Na2SO4, and concentrated to a brown oil which solidified to a brown solid under vacuum (4.5 g, 80% yield): 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.57 (dd, J=7.58, 1.77 Hz, 1 H) 7.35 - 7.41 (m, 1 H) 6.94 - 7.03 (m, 2 H) 5.24 (s, 3 H) 3.89 (s, 3 H),; At O 0C anhydrous ether was introduced to flask under Argon, LiHMDS (94 ml, 93.9 mmol) was then introduced and stirred for 5 mins. 2-Methoxy-benzonitrile (5g, 37.6 mmol) was added and the mixture was stirred at room temperature for 2-3 days. When all the starting material was consumed, solvent was removed and 200 mL cold 1N HCl was added and stirred to make HCI salt. Extracted with Et2O (3X 300 mL) and then pH was adjusted to 13 by 6N NaOH. Extraction with CH2CI2 and dried over Na2SO4. Filtered and the filtrate was concentrated to obtain the above benzamidine compound in 91 % yield.
80% With aluminum (III) chloride; trimethylaluminum; In toluene; at 0 - 70℃; for 16h; Step 1, 2-methoxybeozimidainide: To a stirred solution of ainrnonium chloride (6 g,0.113 mol) in toluene (0 mL) at 0 C was added trimethylaiurniniu (2.97 g, 0.041 mol) drop wise for a period of 10 mm. The reaction mixture was stirred for 3 h at room temperature followed by addition of 2-methoxybenzonitrile (5 g, 0.037 mol) in toluene (10 mL). The reaction was then heated to 70 C for 16 h. After completion, the reaction was quenched with ice cold water, filtered through diatomaceous earth, and washed with ethylacetate. The aqueous layer was extracted with ethyl acetate (2 x). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide a residue. Purification by colunrn chromatography on silica gel (100-200 mesh) using ethyl acetate in hexane afforded the title compound as a solid (4,5 g, 80%).
80% With trimethylaluminum; ammonium chloride; In toluene; at 70℃; for 16h; Step 1. 2-methoxybenzimidamide To a stirred solution of ammonium chloride (6 g, 0.113 mol) in toluene (80 mL) at 0 C. was added trimethylaluminium (2.97 g, 0.041 mol) drop wise for a period of 10 min. The reaction mixture was stirred for 3 h at room temperature followed by addition of 2-methoxybenzonitrile (5 g, 0.037 mol) in toluene (10 mL). The reaction was then heated to 70 C. for 16 h. After completion, the reaction was quenched with ice cold water, filtered through diatomaceous earth, and washed with ethyl acetate. The aqueous layer was extracted with ethyl acetate (2*). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide a residue. Purification by column chromatography on silica gel (100-200 mesh) using ethyl acetate in hexane afforded the title compound as a solid (4.5 g, 80%).
36% With lithium hexamethyldisilazane; In diethyl ether; hexane; at 0 - 20℃; for 24h; To a stirring solution of 2-methoxybenzonitrile 4 (3.00 g, 22.5 mmol) and anhydrous Et20 (50 mL) in a 500 ML three-necked round-bottomed flask equipped with a magnetic stirrer was added lithium HEXAMETHYLDISILAZANE (45.0 ML, 45.0 mmol, 1.0 M in hexane) dropwise over 10 minutes, at 0 C. The solution was stirred at ambient temperature for 24 hours. 2. 0 N aqueous HC1 solution was carefully added dropwise over a 30 minute period at 0 C. The solution was stirred at ambient temperature for 2 hours. The aqueous portion was made strongly basic by the addition of saturated aqueous KOH solution (50 mL). The mixture was extracted with CH2C12 (5 x 40 mL). The organic portions were combined, dried (MGS04), and evaporated to dryness under reduced pressure to obtain 5 (1.20 g, 7. 99 mmol, 36% yield) as a light tan solid. M+1 (obs) = 151. 2; Rt = 0.85.
20% With aluminum (III) chloride; ammonium chloride; In toluene; at 20 - 80℃; for 16.5h;Inert atmosphere; To ammonium chloride (2.16 g, 40 mmol) in toluene (80 mL) was added aluminum chloride (2N in toluene, 20 mL, 40 mmol) dropwise under nitrogen at 0 C. After addition was complete, the mixture was stirred to room temperature for another 30 minutes. To the resulting mixture was added 2-methoxybenzonitrile 16 (5.32 g, 40 mmol) in toluene (20 mL) slowly, then stirred at 80 C for 16 hours. The reaction mixture was cooled to room temperature and poured into a slurry of silica gel (100 g) in chloroform (200 mL). The mixture was stirred for 10 minutes and filtered. The residue was washed with methanol (200 mL) and the combined filtrates concentrated in vacuo. To the resulting residue was added dichloromethane (20 mL), and the mixture filtered to provide 2-methoxybenzimidamide 17 as a white solid (1.2 g, 20%). LCMS analysis of 17: 100% and [M+H]+ = 151.

  • 2
  • [ 54109-16-9 ]
  • [ 51818-19-0 ]
  • 2-(2-methoxyphenyl)-5-(2-(trifluoromethyl)phenyl)-1H-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% To 2-methoxybenzimidamide 17 (150 mg, 1 mmol) and potassium carbonate (414 mg, 3 mmol) in acetonitrile (30 mL) was added 2-bromo-l-(2-(trifluorom ethyl )phenyl)ethan- 1-one 20 (266 mg, 1 mmol) in acetonitrile (10 mL) dropwise at 0 C. The mixture was stirred an additional 2 hours at 0 C, then filtered and concentrated in vacuo. Acetic acid (20 mL) was added to the resulting residue, which was stirred at 60 C overnight. The mixture was concentrated in vacuo to provide a residue that was taken up in saturated aqueous sodium hydrogen carbonate (30 mL) and extracted with ethyl acetate (2 x 30 mL). The combined organic layers were washed with brine (20 mL) and dried over anhydrous sodium sulfate, then concentrated in vacuo to provide a residue that was purified by preparative thin-layer chromatography eluting with dichloromethane to afford 2-(2-methoxyphenyl)-5-(2- (trifluoromethyl)phenyl)-lH-imidazole 21 as a white solid (130 mg, 41%). LCMS analysis of 19: 100% and [M+H]+ = 319.
 

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