ChemicalBook CAS DataBase List alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol

alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol synthesis

11synthesis methods

Product Name:alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanol
CAS Number:24155-42-8
Molecular formula:C11H10Cl2N2O
Molecular Weight:257.12

1-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOLE-1-YL) ETHANONE

46503-52-0

24155-42-8

General procedure for the synthesis of alpha-(2,4-dichlorophenyl)-1H-imidazole-1-ethanol from 2'-(1H-imidazol-1-yl)-2,4-dichloroacetophenone: In a 1000 mL three-necked flask equipped with a stirrer, a thermometer, and a dropping funnel, add 102 g of 2'-(1H-imidazol-1-yl)-2,4-dichloroacetophenone (0.4 mol) and 300 mL of methanol. Potassium borohydride was added in batches and slowly heated to reflux. After completion of the reaction, stirring was continued for 1 h and the progress of the reaction was monitored by thin layer chromatography (TLC) (unfolding agent was ethyl acetate: methanol = 10:1, v/v). At the end of the reaction, methanol was recovered by distillation under reduced pressure. The concentrate was adjusted to pH 4-5 with 5% hydrochloric acid solution and subsequently diafiltrated. The filtrate was adjusted pH to 7-8 with 5% sodium bicarbonate solution, when a white solid precipitated. The solid was collected by filtration, washed with water, dried and recrystallized to give 93.1 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol in 90.5% yield with a melting point of 134-135 °C.

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Yield:24155-42-8 98%

Reaction Conditions:

with sodium tetrahydroborate in ethanol at 20; for 12 h;

Steps:

4.6. General procedure for the synthesis of compounds 10a-10b
General procedure: Sodium borohydride (12 g, 0.3 mol) was added to the ethanolsolution (100 mL) of 9a (25.5 g, 0.1 mol). The mixture was stirred at20 °C for 12 h. Then the water was carefully added to the mixture,the white solid was obtained by filtration and recrystallization(EtOH). Yield 98.0%, HRMS m/z: 257.0217[M+H]+. According to thepreparation method of 10a, 9b was used as raw material to preparethe intermediate 10b: white solid, Yield 97.4%, HRMS m/z: 225.0831[M+H]+.

References:

An, Ran;Guo, Chun;Guo, Meng-bi;Hou, Zhuang;Mou, Yan-hua;Su, Xin;Xu, Hang [European Journal of Medicinal Chemistry,2020,vol. 198]

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288-32-4 Synthesis