67085-12-5

Basic information

• Product Name: 1-(2-Chloro-4-(4-chlorophenyl)butyl)-1H-imidazole
• Synonyms: 1-(2-CHLORO-4-(4-CHLOROPHENYL)BUTYL)-1H-IMIDAZOLE;INTERMEDIATE:BUTOCONAZOLENITRATE
• CAS NO: 67085-12-5
• Molecular Formula: C₁₃H₁₄Cl₂N₂
• Molecular Weight: 269.17
• EINECS: 614-018-7
• Mol File: 67085-12-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 442.6 °C at 760 mmHg
• Flash Point: 221.5 °C
• Appearance: /
• Density: 1.22
• Vapor Pressure: 1.29E-07mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO
• PKA: 6.68±0.12(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 1-(2-Chloro-4-(4-chlorophenyl)butyl)-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Chloro-4-(4-chlorophenyl)butyl)-1H-imidazole(67085-12-5)
• EPA Substance Registry System: 1-(2-Chloro-4-(4-chlorophenyl)butyl)-1H-imidazole(67085-12-5)

Safety Data

• Hazardous Substances Data: 67085-12-5(Hazardous Substances Data)

Usage

Uses

1-[2-Chloro-4-(4-chlorophenyl)butyl]-1H-imidazole is an impurity of Butoconazole (B690273), which is an antifungal.

InChI:InChI=1/C13H14Cl2N2/c14-12-4-1-11(2-5-12)3-6-13(15)9-17-8-7-16-10-17/h1-2,4-5,7-8,10,13H,3,6,9H2

Upstream product

• 59363-13-2 1-chloro-4-(4-chlorophenyl)-2-butanol 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 67085-11-4 1-[2-hydroxy-4-(4-chlorophenyl)-n-butyl]imidazole 

Downstream Products

• 64872-76-0 butoconazole 

Relevant articles and documents

Butoconazole nitrate industrial production method

The invention relates to a method for industrially producing butoconazole nitrate. The method comprises the following steps: (1) taking 1-8 parts of 1-(2-chloro-4-(4-chlorphenyl)butyl)-1-hydro-imidazole, 1-8 parts of 2,6-dichlorothiophenol, 1-5 parts of anhydrous potassium carbonate and 30-50 parts of acetone to undergo heating reflux reaction for 4-6 hours, then replenishing 0.1-1 part of anhydrous potassium carbonate, continuously carrying out heating reflux reaction for 5-9 hours, cooling and filtering the reactant and concentrating the filtrate, thus obtaining a concentrate; (2) taking the concentrate obtained in the step (1), adding extract liquor formed by an organic solvent and water, and after full extraction, retaining an organic phase for later use; (3) dropwise adding concentrated nitric acid to the organic phase obtained in the step (2) and carrying out filtration after stopping generating a precipitate; discarding the filtrate and washing and drying a filter cake, thus obtaining butoconazole nitrate. In the method provided by the invention, the conditions and parameters in the synthetic process are comprehensively and preferentially selected, and the impurities which are likely to be introduced in the production process are effectively controlled, thus increasing the production efficiency and the purity and yield of the product. Therefore, the method is more suitable for large-scale industrial production.

A industrialized production butoconazole nitrate intermediates

The invention relates to a method for industrially producing a butoconazole nitrate intermediate 1-(2-chloro-4-(4-chlorphenyl)butyl)-1-hydro-imidazole. The method comprises the following steps: (1) taking 1-(2-hydroxy-4-(4-chlorphenyl)butyl)-1-hydro-imidazole and thionyl chloride as raw materials to undergo heating reflux in dichloromethane, and after full reaction, cooling the reactant, thus obtaining a reaction liquid; and (2) slowly adding cold water and anhydrous sodium carbonate to the reaction liquid obtained in the step (1) in sequence, carrying out suction filtration, discarding the solid, concentrating the liquid and drying the concentrate, thus obtaining the butoconazole nitrate intermediate. In the method provided by the invention, the conditions and parameters in the synthetic process are comprehensively and preferentially selected, thus increasing the purity and yield of the product. Therefore, the method is more suitable for large-scale industrial production.

Preparation method of butoconazole nitrate

The invention discloses a preparation method of butoconazole nitrate. The preparation method comprises the following steps: with 4-chlorobenzyl chloride as a starting raw material, synthesizing 1-chloro-4-(4-chlorophenyl)-2-butanol, then synthesizing 1-(4-(4-chlorophenyl)-2-hydroxy-butyl) imidazole, then synthesizing 1-(4-(4-chlorophenyl)-2-chloro-butyl) imidazole, adding the 1-(4-(4-chlorophenyl)-2-chloro-butyl) imidazole, 2, 6-dichlorobenzenethiol and potassium carbonate into acetone, heating for refluxing, adding water and ethyl acetate after the completion of a reaction, performing liquid separation, sequentially washing an ethyl acetate phase by using saturated potassium carbonate and saturated salt water, drying by using anhydrous magnesium sulfate, removing magnesium sulfate, dropwise adding nitric acid with the concentration of 65% in an ice bath until no precipitate is produced, filtering for collecting solid, and recrystallizing by using absolute ethanol to obtain white crystals, namely the butoconazole nitrate. By the preparation method of the butoconazole nitrate, the process is simple, the yield is high, the cost is low, and the purity of the obtained product is high.