Identification | Back Directory | [Name]
1-[4-(4-Chlorophenyl)-2-hydroxylbutyl]imidazole | [CAS]
67085-11-4 | [Synonyms]
Butoconazole Impurity 2 Butoconazole Nitrate INT II Butoconazole 2-Hydroxy Impurity 1-[4-(4-Chlorophenyl)-2-hydroxylbutyl] 4-(4-chlorophenyl)-1-imidazol-1-ylbutan-2-ol 1-[4-(4-CHLOROPHENYL)-2-HYDROXYLBUTYL]IMIDAZOLE 4-(4-Chlorophenyl)-1-(1H-iMidazol-1-yl)butan-2-ol 1-[4-(4-chlorophenyl)-2-hydroxy-n-butyl]-imidazole α-[2-(4-Chlorophenyl)ethyl]-1H-imidazole-1-ethanol 1-[4-(4-Chlorophenyl)-2-hydroxyl-n-butyl]imidazole 1H-Imidazole-1-ethanol, α-[2-(4-chlorophenyl)ethyl]- 1-[4-(4-Chlorophenyl)-2-hydroxyl-butyl]-1H-imidazole 1H-IMIDAZOLE-1-ETHANOL,α-[2-(4-CHLOROPHENYL)ETHYL]-(9CI) | [Molecular Formula]
C13H15ClN2O | [MDL Number]
MFCD09751154 | [MOL File]
67085-11-4.mol | [Molecular Weight]
250.72 |
Chemical Properties | Back Directory | [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 |
Hazard Information | Back Directory | [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 |
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