The way to obtain diphenyl-(2-chlorophenyl)methane

IPC classes for russian patent The way to obtain diphenyl-(2-chlorophenyl)methane (RU 2180655):

C07C25/18 - Polycyclic aromatic halogenated hydrocarbons

C07C17/263 -

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(57) Abstract:

The invention relates to a method for producing diphenyl-(2-chlorophenyl)methane to synthesis of 1-(2-chlorophenyl)diphenylmethyl-1H-imidazole with antifungal activity. The method includes the interaction of 2-chlorobenzaldehyde with benzene boiling in an environment of concentrated sulfuric acid until complete consumption of 2-chlorobenzaldehyde.

The invention relates to a method for producing diphenyl-(2-chlorophenyl)methane to synthesis of 1-(2-chlorophenyl)diphenylmethyl-1H-imidazole - antifungal agent.

A method of obtaining diphenyl (2-chlorophenyl)methane by reacting diphenyl (2-chlorophenyl)methanol with iodine and red phosphorus in the environment of acetic acid by boiling for 24 hours. From the reaction mixture the product is extracted with benzene, the extract was concentrated in vacuo and then distilled selected fraction with a boiling point 191-197^oWith 7 mm RT.article The target product is a white crystals with a melting point 75-77^oWith, the product yield is 47.5% (see Bradsher, C. K., Smith, A. S. J. Am. Chem. Soc., 1943, vol. 65, R. 451-452).

A method of obtaining diphenyl (2-chlorophenyl)methane by interacting with idiscovered the m hydrogen iodide and added to a solution of diphenyl (2-chlorophenyl)methanol in acetic acid. Boil, then the product is extracted with ether, neutralized. Separate the ether and get the target product with a melting point 77^oC.

The closest in technical essence is a method for production of diphenyl (2-chlorophenyl)methane by reacting organic chemicals when heated, which as organic reagents take diphenyl (2-chlorophenyl)methanol with formic acid. The process is carried out by boiling the initial reagents, the product is extracted with ether, neutralized, separate the ether and get the desired product in the form of oil, which, when the rubbing wand crystallizes (melting point 76-77^oC), the product yield is 76% (see Rec. Trav. Chim. Pays-Bas, 1915, vol. 34, R. 168).

A disadvantage of known methods is that the original substance (organic reagent) - diphenyl (2-chlorophenyl)methanol industry is not available, the method for obtaining multi-stage, involves the use of flammable magnesium, organolithium compounds and volatile solvents (see patent 2102373 RF, C1/B. I., 2, 1998).

The task of the invention is to simplify the method and the expansion of the means of obtaining diphenyl (2-chlorophenyl)-methane.

Technical ass is the agrevanie, as organic reagents take 2-chloro-benzaldehyde from benzene, the process is conducted in an environment of concentrated sulfuric acid until complete consumption of 2-chlorobenzaldehyde.

Technical solution allows to simplify the way through the use of commercially available source of organic chemicals produced in one stage from the available raw materials, and to expand the Arsenal of means to obtain diphenyl (2-chloro-phenyl)methane.

The characteristics of the original components.

2-Chlorobenzaldehyde is colorless transparent liquid, melting point 10^oC, boiling point 87^oWith a density of 1.25 g/cm³TU 6-09-15-518-82.

Benzene is a colorless liquid with a characteristic odor, melting point of 5.5^oC, the boiling point of 80.1^oWith a density of 0,879 g/cm³, GOST 5955-75.

Sulphuric acid is a colourless, oily liquid, odorless, mass fraction of the main substances 93,6-95,6 %, GOST 4204-77.

The structure of the target product proved NMR data¹N spectroscopy, confirmed by the results of elemental analysis.

This invention is illustrated by the following examples of specific performance.

Example 1. Use their reagents are in 21 g (0.2 mole) of concentrated sulfuric acid at boiling benzene until complete consumption of 2-chlorobenzaldehyde (control is carried out on the spectrum of TMR). Then the benzene layer washed with water, neutralized. The excess benzene is distilled off and produce the product in the form of white crystals with a melting point 77^oC (lit. 76-77^oC). Yield: 85%. An NMR spectrum¹N (, m D.) (CCl₄):5,9 (1H, C-H), 7,4-6,8 (14N, m, arene.).

The data of elemental analysis (%).

Calculated: 81,70; N 5,47; Cl 12,63.

Received: From 81,75; N. Of 5.45; Cl 12,65.

Example 2. Analogously to example 1, but the reaction is carried out with stoichiometric amounts of reagents. Yield: 55%.

Example 3 (the prototype). The method carried out in laboratory conditions. Dissolve 2.9 g (0,01 mol) diphenyl (2-chlorophenyl)-methanol in 10 ml of anhydrous formic acid. Boil for 1 hour, then dissolved in ether. The ether solution is washed with water, 0.5 M KOH solution, again with water. Dried over CaCl₂then distilled off ether and produce the product in the form of oil, which, when the rubbing wand crystallizes. After recrystallization from hexane obtain 2.1 g of pure diphenyl (2-chlorophenyl)methane with a melting point 76^oC. Yield: 76.6 Per Cent.

A method for production of diphenyl(2-chlorophenyl)methane by the reaction of 2-chlorobenzaldehyde with benzene boiling in an environment of concentrated sulfuric acid to