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CAS No. : | 57075-83-9 | MDL No. : | MFCD06738644 |
Formula : | C8H11ClN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 186.64 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
61% | With potassium phosphate; oxygen; copper diacetate In toluene at 100℃; for 10h; |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate; In methanol; at 18.6 - 65℃;Inert atmosphere; | Example 1F 4-(dimethoxymethyl)-2-(2-methoxyphenyl)pyrimidine An oven-dried 5 L three neck flask equipped with a mechanical stirrer, nitrogen inlet into a reflux condenser and outlet to a bubbler, and an internal temperature probe (J-KEM controlled), was charged with Example 1E (126.9 g) and <strong>[67751-23-9](E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one</strong> (177 g). Anhydrous methanol (1360 mL) was added. To the mixture at room temperature under nitrogen was added solid sodium methoxide (257 g) in portions over 20 minutes. The temperature of the reaction went up from 18.6 C. to 35.7 C. during the addition. Once the exotherm stopped, the reaction mixture was heated to 65 C. overnight. The reaction mixture was cooled, and concentrated. The residue was mixed with ethyl acetate (800 mL), and water (1 L) was added carefully. The two phase mixture was sonicated for about 30 minutes to dissolve all the material. The layers were separated, and organic layer was washed with saturated aqueous NH4Cl mixture. The combined aqueous extracts were extracted one time with ethyl acetate. The combined organic extracts were washed with brine, dried with Na2SO4, filtered, and concentrated. The residue was dissolved in a small amount of dichloromethane (30 mL) and loaded onto a 2.0 L plug of silica in a 3 L Buchner funnel that had been equilibrated with 40% ethyl acetate/heptane. The desired product was eluted with 40% to 50% ethyl acetate/heptane. The fractions containing the desired product were combined, and were concentrated to provide the title compound. 1H NMR (500 MHz, dimethyl sulfoxide-d6) delta ppm 8.93 (d, 1H), 7.54 (dd, 1H), 7.50-7.43 (m, 2H), 7.16 (dd, 1H), 7.06 (td, 1H), 5.31 (s, 1H), 3.76 (s, 3H), 3.38 (s, 6H). MS (DCI) m/z 261.0 (M+H)+. | |
In methanol; at 18.6 - 65℃;Reflux; Inert atmosphere; | An oven-dried 5 L three neck flask equipped with a mechanical stirrer, nitrogen inlet into a reflux condenser and outlet to a bubbler, and an internal temperature probe (J-KEM controlled), was charged with Example I 8C (126.9 g) and (E)-4-(dimethylamino)- I, 1-dimethoxybut-3-en-2-one (177 g).Anhydrous methanol (1360 mL) was added. To the mixture at room temperature under nitrogen was added solid sodium methoxide (257 g) in portions over 20 minutes. The temperature of the reaction went up from 18.6 C to 35.7 C during the addition. Once the exotherm stopped, the reaction mixture was heated to 65 C overnight. The reaction mixture was cooled, and concentrated. The residue was mixed with ethyl acetate (800 mL), and water (1 L) was added carefully. The two phase mixture was sonicatedfor about 30 minutes to dissolve all the material. The layers were separated, and organic layer was washed with saturated aqueous NH4CI mixture. The combined aqueous extracts were extracted one time with ethyl acetate. The combined organic extracts were washed with brine, dried with Na2SO4, filtered, and concentrated. The residue was dissolved in a small amount of dichloromethane (30 mL) and loaded onto a 2.0 L plug of silica in a 3 L Buchner funnel that had been equilibrated with 40% ethylacetate/heptane. The desired product was eluted with 40% to 50% ethyl acetate/heptane. The fractions containing the desired product were combined, and were concentrated to provide the title compound. ?H NMR (500 M1-{z, dimethylsulfoxide-d6) 6 ppm 8.93 (d, lH), 7.54 (dd, lH), 7.50-7.43 (m, 2H), 7.16 (dd, lH), 7.06 (td, IH), 5.31 (s, IH), 3.76 (s, 3H), 3.38 (s, 6H). MS (DCI) m/z 261.0 (M+H). |
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