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

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

Used in Pharmaceutical Industry:
1-(2-Chloro-4-(4-chlorophenyl)butyl)-1H-imidazole is used as an impurity in the antifungal drug Butoconazole (B690273). Its presence in the drug formulation is significant as it can affect the overall efficacy and safety profile of the medication. As an impurity, it is essential to monitor and control its levels to ensure the quality and consistency of the antifungal treatment.
In the context of its use as an impurity in Butoconazole, 1-(2-Chloro-4-(4-chlorophenyl)butyl)-1H-imidazole serves as a critical component in the development and production of antifungal medications. Its role in the pharmaceutical industry highlights the importance of understanding and managing impurities in drug formulations to maintain the desired therapeutic effects and minimize potential side effects.

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-chlorine-4-(4-chlorphenyl) butyl)-1hydrogen-imidazole. The method comprises steps as follows: (1), 2-5 parts of 1-(2-hydroxyl-4-(4-chlorphenyl) butyl)-1hydrogen-imidazole is taken and sufficiently dissolved in 20-40 parts of dichloromethane, 2-5 parts of thionyl chloride are slowly and dropwise added at the temperature of 15 DEG C-25 DEG C, the mixture is slowly heated to 25 DEG C-65 DEG C for a sufficient reaction and cooled, and a reaction liquid is obtained; (2), cold water and anhydrous sodium carbonate are sequentially and slowly added to the reaction liquid obtained in the step (1), suction filtration is performed, solids are abandoned, a liquid is concentrated and dried, and the butoconazole nitrate intermediate is obtained. According to the provided method, conditions and parameters in the synthesis process are comprehensively and preferentially selected, the purity and the yield of products are improved, and 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.

Butoconazole nitrate industrial production method

The invention relates to a method for producing butoconazole nitrate. The method comprises the following steps: (1) taking 1-(2-chloro-4-(4-chlorphenyl)butyl)-1-hydro-imidazole, 2,6-dichlorothiophenol and anhydrous potassium carbonate as raw materials to undergo heating reflux in acetone, after full reaction, cooling and filtering the reactant and concentrating the filtrate, thus obtaining a concentrate; (2) taking the concentrate obtained in the step (1) and adding extract liquor which comprises diethyl ether and water in a weight ratio of (2-3) to (1-2); after full extraction, discarding a water phase and 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.

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.

Method for industrial process production of butoconazole nitrate

The invention relates to a method for industrial process production of butoconazole nitrate. The method comprises the step that an intermediate product 1-chlorine-4-(4-chlorphenyl)-2-butanol, an intermediate product 1-(2-hydroxy-4-(4-chlorphenyl)butyl)-1 hydrogen-imidazole, an intermediate product 1-(2-chlorine-4-(4-chlorphenyl)butyl)-1 hydrogen-imidazole, a butoconazole nitrate crude product and a butoconazole nitrate finished product are sequentially synthesized. According to the method, conditions and parameters in the synthesizing process are comprehensively optimized, impurities likely to be introduced in the production process are effectively controlled, the production efficiency is improved, the purity and yield of the products are increased, and the method is suitable for industrial production.

HIGH PURITY BUTOCONAZOLE NITRATE WITH SPECIFIED PARTICLE SIZE AND A PROCESS FOR PREPARATION THEREOF

One object of the invention is high purity butoconazole nitrate of the formula (I) (I) containing maximum 0.1 wt % of chemical impurities, wherein at least 95% of the particles of the substance are below 75μm by diameter, whereas at least 99% of the particles are below 250μm by diameter, and process for its preparation. A pharmaceutical composition comprising as active ingredient, high purity butoconazole nitrate of specified particle size in admixture with known auxiliaries is also within the scope of the invention.

Derivatives of thienyl- and furyl-substituted N-butyl and N-phenyl imidazoles

The compounds of the present invention are represented by the formula STR1 wherein R1 and R2 are the same or different and are optionally substituted furyl or thienyl the substituents independently selected from the group halo, C1 to C6 alkyl and C1 to C6 alkoxy or optionally substituted phenyl the substituents independently selected from the group halo, C1 to C4 alkyl, C1 to C4 alkoxy and trifluoromethyl; X is oxygen or sulfur; m is the integer 0; and n is the integer 2 or 3; and the antimicrobial acid addition salts thereof, with the proviso that when either R1 or R2 is said optionally substituted phenyl the other R1 or R2 is said optionally substituted furyl or thienyl. The compounds are useful for combatting fungi, bacteria and protozoa. They also have spermatocidal and spermatostatic activity.

Derivatives of substituted N-alkyl imidazoles and compositions and methods containing the same

Compounds of the formula STR1 wherein R1 is phenethyl and R2 is phenyl, each of said phenethyl or phenyl independently being unsubstituted or substituted in the phenyl ring by from 1 to 3 substituents selected from the group consisting of halo, lower alkyl and lower alkoxy with the proviso that at least one of R1 and R2 be substituted by lower alkoxy; X is oxygen or sulfur; and the antimicrobial acid addition salts thereof are useful as antifungal, antibacterial and antiprotozoal agents.