Benzimidazole compound and preparation method and application thereof
A technology of benzimidazole and phenyl, which is applied in the field of chemical synthesis and can solve problems such as long reaction time
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[0062] see Figure 1-3 , The preparation method of 2-substituted-N-[5-(2-amino-1,3,4-thiadiazole)-methylene]-benzimidazole of the present invention comprises the following steps:
[0063] 1) The benzimidazole compound of Amol and the potassium chloroacetate of Bmol are mixed and dissolved in ethanol, then water is added therein, stirred and heated to reflux state, monitor the reaction with TLC in the reflux reaction process completely, after the reaction finishes, the obtained The reaction solution was cooled to room temperature, and the pH value of the reaction solution was adjusted to 1-2 with hydrochloric acid with a mass concentration of 37.5% in an ice-water bath. At this time, a solid precipitated, and after the solid was separated, it was recrystallized with absolute ethanol and water to obtain 1 -carboxymethylbenzimidazoles (reaction scheme sees figure 1 ); Wherein, A:B=1:(1-1.5); Every mole of benzimidazole is dissolved in the ethanol of 4~5L; The developing agent th...
Embodiment 1
[0088] 1) Add 0.005mol benzimidazole, 20mL ethanol, 0.007mol potassium chloroacetate to a clean 100mL three-necked flask in turn, and dissolve them in water, then heat up to reflux state under stirring, monitor the reaction process with TLC during the reflux reaction, and the reaction is over Finally, the obtained reaction solution was cooled to room temperature, and the pH value of the reaction solution was adjusted to 1-2 with hydrochloric acid with a mass concentration of 37.5% in an ice-water bath. At this time, a large amount of solids were precipitated, and suction filtration was performed with a volume ratio of 1:1. A mixed solvent of ethanol and water was used for recrystallization, and after standing overnight, suction filtration and drying gave 0.65 g of white solid 1-carboxymethylbenzimidazole, and the developer used for TLC monitoring was ethyl acetate with a volume ratio of 1:3 It is mixed with petroleum ether; the yield is 73.5%, m.p.: 299-300°C. IR (KBr pellet, ...
Embodiment 2
[0093] 1) Add 0.005mol 2-methylbenzimidazole, 20mL ethanol, 0.007mol potassium chloroacetate to a clean 100mL three-necked flask, and dissolve them in water, then heat up to reflux under stirring, monitor the reaction process with TLC during the reflux reaction After the reaction, the reaction solution obtained is cooled to room temperature, and the pH value of the reaction solution is adjusted to 1-2 with hydrochloric acid with a mass concentration of 37.5% under an ice-water bath. At this time, a large amount of solids are precipitated, and suction filtration is performed with a volume ratio of A 1:1 mixed solvent of ethanol and water was used for recrystallization. After standing overnight, suction filtration and drying gave 0.19 g of 1-carboxymethyl-2-methylbenzimidazole. The developer used for TLC monitoring had a volume ratio of 1 : 3 mixed with ethyl acetate and petroleum ether; the yield is 40.2%, m.p.: >300°C. IR (KBr pellet, ν / cm -1 ): 1720, 1618, 1585, 1462, 1384. ...
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