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Chemical Structure| 57075-83-9

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Product Details of [ 57075-83-9 ]

CAS No. :57075-83-9
Formula : C8H11ClN2O
M.W : 186.64
SMILES Code : N=C(N)C1=CC=CC=C1OC.[H]Cl
MDL No. :MFCD06738644

Safety of [ 57075-83-9 ]

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

Application In Synthesis of [ 57075-83-9 ]

* 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 [ 57075-83-9 ]

[ 57075-83-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 6609-56-9 ]
  • [ 57075-83-9 ]
YieldReaction ConditionsOperation in experiment
With trimethylaluminum; ammonium chloride; In toluene; at 90℃; Example 1E 2-methoxybenzimidamide hydrochloride A dried 12 L five-necked flask equipped with a mechanical stirrer, a gas inlet with tubing leading to a nitrogen regulator, a gas inlet adapter with tubing leading to a bubbler, and an internal temperature probe (J-KEM controlled), was charged with ammonium chloride (86 g). The material was mixed under nitrogen with anhydrous toluene (2 L). The mixture was cooled to -12.3 C. in an ice/methanol bath. To the mixture was added, via cannula, 2.0 M trimethylaluminum in toluene (800 mL). Upon addition of the trimethylaluminum, the mixture started to smoke immediately and gas was evolved. The temperature of the reaction mixture rose to a high of -0.4 C. during the addition, and the addition took a total of about 60 minutes. After all the trimethylaluminum was added, the mixture was allowed to stir at 20 C. for 3 hours. To the mixture was added 2-methoxybenzonitrile (107 g) as a liquid (had been melted in bath at about 45 C.). Once the 2-methoxybenzonitrile was added, the reaction mixture was heated at 90 C. overnight with the use of a heating mantle controlled by a J-KEM. The reaction flask was fitted with a vigreux condenser. Thin-layer chromatography in 50% ethyl acetate/heptane indicated a major baseline product. The reaction mixture was cooled to -8.7 C. in an ice/methanol bath, and to the cold mixture was added 4 L of methanol, dropwise via an addition funnel. The addition evolved gas and was exothermic. The temperature of the reaction mixture reached a high of 7.9 C., and the addition took a total of about one hour. After all the methanol was added, the mixture was allowed to stir for three hours at 20 C. The reaction mixture was filtered through filter paper on a benchtop filter. The material collected were washed with additional methanol (2 L). The filtrate was concentrated. The crude material was mixed with 500 mL of ethyl acetate. The mixture was sonicated for 30 minutes and was stirred for another 30 minutes. The material was filtered off and washed with more ethyl acetate. The material collected was air dried for an hour and then dried under high vacuum for two hours to provide the title compound. 1H NMR (400 MHz, dimethyl sulfoxide-d6) δ ppm 9.23 (bs, 2H), 7.69 (bs, 1H), 7.63 (ddd, 1H), 7.55 (dd, 1H), 7.25 (dd, 1H), 7.12 (td, 1H), 3.87 (s, 3H). MS (DCI) m/z 151.0 (M+H)+.
With trimethylaluminum; ammonium chloride; In toluene; at -12.3 - 90℃;Inert atmosphere; A dried 12 L five-necked flask equipped with a mechanical stirrer, a gas inlet with tubingleading to a nitrogen regulator, a gas inlet adapter with tubing leading to a bubbler, and an internaltemperature probe (J-KEM controlled), was charged with ammonium chloride (86 g). The material was mixed under nitrogen with anhydrous toluene (2 L). The mixture was cooled to -12.3 C in an ice/methanol bath. To the mixture was added, via cannula, 2.0 M trimethylaluminum in toluene (800 mL). Upon addition of the trimethylaluminum, the mixture started to smoke immediately and gas wasevolved. The temperature of the reaction mixture rose to a high of-0.4 C during the addition, and the addition took a total of about 60 minutes. After all the trimethylaluminum was added, the mixture was allowed to stir at 20 C for 3 hours. To the mixture was added 2-methoxybenzonitrile (107 g) as a liquid (had been melted in bath at about 45 C). Once the 2-methoxybenzonitrile was added, the reaction mixture was heated at 90 C overnight with the use of a heating mantle controlled by a J-KEM. Thereaction flask was fitted with a vigreux condenser. Thin-layer chromatography in 50% ethyl acetate/heptane indicated a major baseline product. The reaction mixture was cooled to -8.7 C in an ice/methanol bath, and to the cold mixture was added 4 L of methanol, dropwise via an addition funnel. The addition evolved gas and was exothermic. The temperature of the reaction mixture reached a high of 7.9 C, and the addition took a total of about one hour. After all the methanol was added, the mixturewas allowed to stir for three hours at 20 C. The reaction mixture was filtered through filter paper on a benchtop filter. The material collected were washed with additional methanol (2 L). The filtrate was concentrated. The crude material was mixed with 500 mL of ethyl acetate. The mixture was sonicated for 30 minutes and was stirred for another 30 minutes. The solids material was filtered off and washed with more ethyl acetate. The material collected were air dried for an hour and then dried under high vacuum for two hours to provide the title compound. ‘H NMR (400 MHz, dimethylsulfoxide-d6) 6 ppm 9.23 (bs, 2H), 7.69 (bs, IH), 7.63 (ddd, IM), 7.55 (dd, IH), 7.25 (dd, IH), 7.12 (td, IH), 3.87 (s, 3H). MS (DCI) m/z 151.0 (M+H).
 

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