1-[4-(4-Chlorophenyl)-2-hydroxylbutyl]imidazole Chemical Properties

Melting point:

106-109 °C(Solv: ethyl acetate (141-78-6))

Boiling point:

472.2±40.0 °C(Predicted)

Density 

1.21±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO, Methanol (Slightly)

form 

Solid

pka

13.69±0.20(Predicted)

color 

White to Off-White

1-[4-(4-Chlorophenyl)-2-hydroxylbutyl]imidazole Usage And Synthesis

Uses

α-[2-(4-Chlorophenyl)ethyl]-1H-imidazole-1-ethanol is used as a reactant in the preparation of imidazol phenylbutane derivatives as heme oxygenase inhibitors. α-[2-(4-Chlorophenyl)ethyl]-1H-imidazole-1-ethanol is also an impurity of Butoconazole (B690273), which is an antifungal.

Synthesis

(2) In a dry DMF solvent, sodium hydride (in the form of mineral oil dispersion) at a concentration of 20% was added and 20 mL of a DMF solution of imidazole was added dropwise at a rate of 2 mL/s under ice bath cooling conditions. Subsequently, the reaction mixture was stirred at 60 °C for 60 min. After the ice bath was cooled, Intermediate 1 (weight ratio of imidazole, sodium hydride to Intermediate 1 was 7:7:5) was slowly added via the salt bath method. The reaction mixture was continued to be stirred at 60°C for 120 minutes. After completion of the reaction, the reaction was again cooled in an ice bath and a 25% n-hexane solution was added to the reaction mixture and stirred at a rate of 3 rev/s for 15 min. Subsequently, ice (350% by weight of the reaction mixture) was added and stirring was continued at a rate of 3 rev/s until the precipitation was complete. The precipitate was collected by filtration and the filter cake was washed once with water and then dried by centrifugation at 2830 r/min for 60 minutes. The resulting product was treated with 2.5 times its weight of ethyl acetate and 0.05 times its weight of activated charcoal, left to stand at 5 °C for 13 h, followed by recrystallization at 50 °C. The yield of Intermediate 2 was 71.5% by HPLC analysis, wherein the purity of the target product 1-[4-(4-chlorophenyl)-2-hydroxy-n-butyl]imidazole was 99.31%.

References

[1] Patent: CN105218455, 2016, A. Location in patent: Paragraph 0055
[2] Patent: CN105175341, 2017, B. Location in patent: Paragraph 0048-0052
[3] Patent: CN105175338, 2018, B. Location in patent: Paragraph 0069-0071
[4] Patent: CN107501190, 2017, A. Location in patent: Paragraph 0033; 0036; 0043; 0046
[5] Patent: WO2005/70897, 2005, A1. Location in patent: Page/Page column 7

1-[4-(4-Chlorophenyl)-2-hydroxylbutyl]imidazole(67085-11-4)Related Product Information

• tert-Butyldimethylsilyl chloride
• Butylated hydroxyanisole
• Imidazole
• Chlorodimethylphenylsilane
• Triphenylmethyl Chloride
• Butylated Hydroxytoluene
• tert-Butylchlorodiphenylsilane
• p-Chlorophenylbutylene oxide
• 1-(2-Chloro-4-(4-chlorophenyl)butyl)-1H-imidazole
• Butoconazole Impurity
• 1-Chloro-4-(4-chlorophenyl)-2-butanol
• Butoconazole Impurity 5 HCl
• CHLOROPHENYLSILANE
• Butoconazole Impurity 9
• Butoconazole Impurity 10
• Butoconazole Impurity 8
• Butoconazole Impurity 7
• azalanstat