CS247581B1 - N-oxides 2- (monosubstituted phenyl) -3-dodecyl-5-chloromethyloxazolidines and the method for their preparation - Google Patents

Abstract

The aim of the solution is to prepare new improved disinfectants. The stated purpose is achieved by N-oxides of 2-/monosubstituted phenyl/-3-dodecyl-5-chloromethyl oxazolidines of the general formula I, where R represents hydrogen, hydroxy, methoxy, bromine, chlorine, and a nitro group in position 2, or 3, or 4. The stated purpose is achieved by a method for preparing these compounds, which consists in treating 2-/monosubstituted phenyl/-3-dodecyl-5-chloromethyl oxazolidine with an aqueous solution of hydrogen peroxide at a temperature of 50 to 60 ° C. N-oxides of 2-monosubstituted phenyl-3-dodecyl-5-chloromethyl oxazolidines and a method for their preparation have application in detergent compositions, in washing and simultaneous disinfection of rooms, tools and in washing textiles.

Description

(54) N-oxides of 2-(monosubstituted phenyl)-3-dodecyl-5-chloromethyloxazolidines and process for their preparation

The aim of the solution is to prepare new improved disinfectants. The stated purpose is achieved by N-oxides of 2-/monosubstituted phenyl/-3-dodecyl-5-chloromethyloxazolidines of the general formula I, where R represents hydrogen, hydroxy, methoxy, bromine, chlorine, and a nitro group in position 2, or 3, or 4. The stated purpose is achieved by a method for preparing these compounds, which consists in treating 2-/monosubstituted phenyl/-3-dodecyl-5-chloromethyloxazolidine with an aqueous solution of hydrogen peroxide at a temperature of 50 to 60 ° C. N-oxides of 2-monosubstituted phenyl-3-dodecyl-5-chloromethyloxazolidines and a method for their preparation have application in detergent compositions, in washing and simultaneous disinfection of rooms, tools and in washing textiles.

The invention relates to N-oxides of 2-(monosubstituted phenyl)-3-dodecyl-5-chloromethyloxazolidines and a process for their preparation.

In recent years, a number of articles have appeared in the scientific literature dealing with oxazolidine derivatives and their bactericidal, virucidal and fungicidal properties. For example, 2,2-dibenzyl-4,4-dimethyloxazolidines have shown virucidal properties [ W. De Luca,

A. Keith, W. Snipes: Antimicrob. Agents Chemother. 63 /1980/], which was effective against Herpes simplex.

Derivatives of 4,4-dimethyloxazolidine were active against influenza viruses [^J. H. Hunsucker: Chem. Abstr. 89, 141895v /1978/]. Bactericidal activity was found in 3-alkyloxazolidines [e. Boerner, Η. N. Stracke, V. Wehle: Chem. Abstr. 89, 16U923q /1978/j H. Schnegelberger,

H. Bellinger: Chem. Abstr. 80, 52284s /1974/; K. Bansemir, H. Bellinger, K. Disch: Chem. Abstr. 92, 215428Í /1980/], 2-piperonyl oxazolidines [s. I. Sadych, A. B. Aliev, R. M. Mustafaev: Azerb. Chim. Z. 56 /1972/], 3-alkyl-4-hydroxymethyl-4-methyl oxazolidines [^M. Jarcho: Chem. Abstr. 58, 166772b /1983/]] and others. Of the fungicidal derivatives of oxazolidine, we mention 2-phenyl-3-cyclooctyloxazolidine |]firma BASF A. G.: Chem. Abstr. 58, 4582a /1963/].

However, these derivatives had the disadvantage of being insoluble in water, which limited their use. The attachment of a quaternary ammonium group to the oxazolidine skeleton increased the solubility of these substances in water, but also reduced their biocidal activity. Another disadvantage of these quaternary ammonium salts is that they are not miscible with most commercially available surfactants.

These disadvantages are eliminated by the present invention. The essence of the invention is the N-oxides of 2-(monosubstituted phenyl)-3-dodecyl-5-chloromethyloxazolidines of the general formula I

HjC , °r l

Η ₃ ε(εΗ ₂ ) _1Ί Ν chch ₂ ci

/1/ where R represents hydrogen, hydroxy, methoxy, bromine, chlorine and nitro in position 2, or 3, or 4. Furthermore, the invention provides a method for preparing compounds of general formula I, which consists in reacting 2-(monosubstituted phenyl)-3-dodecyl-5-chloromethyloxazolidine of general formula II

where R represents hydrogen, hydroxy, methoxy, bromine, chlorine and nitro in position 2, or 3, or 4, is treated with an aqueous solution of hydrogen peroxide in ethanol at a temperature of 50 to 60 °C.

The advantage of these substances is their solubility in water, stability in aqueous solutions, high foaming, detergent, bactericidal and fungicidal properties.

Example 1

3.65 g (0.01 mol) of 2-phenyl-3-dodecyl-5-chloromethyloxazolidine is added to 20 ml of ethanol. After the oxazolidine has dissolved, 20 ml of a 30% by weight aqueous solution of hydrogen peroxide is added. The reaction mixture is heated at 60 °C under a reflux condenser for 2 hours. It is then left to stand for 10 hours at 20 to 30 °C. After the reaction is complete, 0.05 g of platinum dioxide is added, which decomposes the excess hydrogen peroxide. The mixture is stirred on an electromagnetic stirrer for 24 hours and the platinum dioxide is filtered off (after washing with ethanol and drying it can be reused).

Unreacted oxazolidine is removed from the reaction mixture by extraction with 10 ml of butanol.

The aqueous layer is azeotropically distilled at 3 kPa and 40 °C to dryness after adding another 10 ml of butanol. A 92% yield was obtained, i.e. 3.5 g of 2-phenyl-3-dodecyl-5-chloromethyloxazolidine N-oxide, which is a non-distillable light yellow oily liquid. In aqueous solutions it is stable at pH 7 up to temperatures above 30 °C.

The infrared spectrum had the following characteristic absorption bands: 2920, 2855, 1590, 1470, 1170, 1126 and 960 cm h. The mass spectrum had the following characteristic peaks: 293, 291, 242, 240, 228, 226, 197, 106, 104.

Elemental analysis for C _2n H ₃₆ NO ₂ Cl, molecular weight 381.5

calculated: 69.20% by weight carbon, 9.44% by weight nitrogen, hydrogen 3Γ67% mass found: 69.08% mass carbon, 9.49% by weight hydrogen 3.63% mass nitrogen.

N-oxide of 2-phenyl-3-dodecyl-5-chloromethyloxazolidine had bacteriostatic and fungistatic activity on microorganisms Staphylococcus aureus, Staphylococcus epidermidis 1ug.ml ^-1 , on microorganisms Bacillus subtilis, Streptococcus faecalis, Microsporum gypsaeum, Trichophyton terrestre and Epidermaphyton 10 ug.ml \ on microorganisms Escherichia coli, Shigella flexneri, Candida, albicans and Saccharomyces cerevisiae 100/ug.ml ^-1 .

Example 2

The procedure is as in Example 1 except that 3.81 g of 2-(2-hydroxyphenyl)-3-dodecyl-5-chloromethyloxazolidine are used. The yield is 86.8%, i.e. 3.45 g of 2-(2-hydroxyphenyl)-3-dodecyl-5-chloromethyloxazolidine N-oxide.

The infrared spectrum shows the following characteristic absorption bands: 2930, 2860, 1590, 1470, 1210, 1120, 1098, 965 cm ¹ . The mass spectrum shows the following characteristic peaks: 293, 291, 258, 256, 244, 242, 197, 106, 104.

Elemental analysis for C ₂ U _J6 i4O ₃ Cl, molecular weight 397.5

calculated: 66.42% by weight, 3.52% by weight, . carbon, . nitrogen 9.U6% by weight hydrogen. found: . 66.05* % by weight, . carbon. 9.17% by weight hydrogen, 3., 48 wt., . nitrogen. - - Bacteriostatic and antifungal efficacy was tested for Staphylococcus aureus microorganisms..

Staphylococcus epidermidis', btreptocoeous raocalis 10 ug.ml', on Microsporum gypsaeum. in ^{Λ 1} · -......

and Epidermaphyton luu'

Example 3

The procedure is as in Example 1 except that 3.96 g of 2-(4-methoxyphenyl)-3-dodecyl-5-chloromethyloxazolidine are used. The yield is 94.8%, i.e. 3.90 g of 2-(4-methoxyphenyl)-3-dodecyl-5-chloromethyloxazolidine N-oxide.

The infrared spectrum had the following characteristic bands: 2850, 1585, 1470, 1260, 1100, 1095, 1045, 965 om ^-1 . The mass spectrum had the following characteristic peaks: 293, 291, 272", 270, 258, 256, 197, 106, 104.

Elemental analysis for ^C 23 ^H 38 ^NO 3 ^C1 ' molecular weight 411.5 calculated: 67.07 wt % carbon, 9.23 wt % hydrogen,

3.40 wt. % nitrogen found: 66.94 wt. % carbon, 9.36 wt. % hydrogen,

3.36% by weight nitrogen.

The bacteriostatic and fungistatic activity on the microorganisms Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus faecalis and Bacillus subtilis was 10 µg.ml, on Candida albicans and Epidermaphyton 100 µg.ml ^-1 .

Example 4

The procedure is as in Example 1 except that 4.44 g of 2-(3-bromophenyl)-3-dodecyl-5-chloromethyloxazolidine are used. The yield is 92.3%, i.e. 4.25 g of 2-(3-bromophenyl)-3-dodeoyl-5-chloromethyloxazolidine N-oxide.

The following were the characteristic absorption bands in the infrared spectrum: 2850, 1580, 1470, 1105, 1090, 960, 580 cm ⁴ . The following were the characteristic peaks in the mass spectrum: 382, 380, 321, 319, 307, 305, 293, 291, 289, 197, 106, 104.

Elemental analysis for ^C 22 ^H 35 ^NO 2 ^BrC ·''' molecular weight 460.5 calculated: 57.33 wt% carbon, 7.60 wt% hydrogen,

3.04 wt. % nitrogen found: 57.00 wt. % carbon, 7.82 wt. % hydrogen,

2.97% by weight of nitrogen.

The bacteriostatic and fungistatic effect on the microorganisms Staphylococcus aureus, Staphylococcus epidermidis, Trichophyton terrestre, Candida albicans and Epidermaafcyton was 100 /ug-ml

Example 5

The procedure is as in Example 1 except that 4 g of 2-(4-chlorophenyl)-3-dodecyl-5-chloromethyloxazolidine are used. The yield was 95.2%, i.e. 3.96 g of 2-(4-chlorophenyl)-3-dodecyl-5-chloromethyloxazolidine N-oxide.

The following were the determining absorption bands in the infrared spectrum: 2855, 1575, 1470, 1118, 1095, 1088, 960, 720 cm ^-1 . The following were the determining peaks in the mass spectrum: 293, 291, 277, 276, 274, 262, 261, 260, 246, 245, 244, 197, 106, 104.

Elemental analysis for C ₂₂ H ₃₃ NO ₂ C1 ₂ , molecular weight 416 i

calculated: 63.46 3.37 % wt. % wt. carbon, 8.41% by weight hydrogen, nitrogen. found: 63.39 % mass carbon, 8.50 % mass of hydrogen, 3.32 % mass nitrogen.

Bacteriostatic and fungistatic activity was 10/Ug-ml ^-1 on microorganisms Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, Trichophyton terrestre, Candida albicans and Epidermaphyton, 100 ug.ml ^-1 .

Example 6

The procedure is as in Example 1 except that 4.1 g of 2-(2-nitrophenyl)-3-dodecyl-5-chloromethyloxazolidine are used. The yield is 93.8% and 4.00 g of 2-(2-nitrophenyl)-3-dodecyl-5-chloromethyloxazolidine N-oxide.

The following were the determining absorption bands in the infrared spectrum: 2850, 1580, 1475, 1380, 1120, 1088, 955, 880 cm ¹ . The following were the determining peaks in the mass spectrum: 293, 291, 287, 285, 273, 271, 257, 255, 197, 106, 104.

Elemental analysis for C ₂₂ H ₃₅ N ₂ O ₄ C1, molecular weight 426.5 *

calculated: 61.90% by weight 6.57% by weight carbon, 8.21 nitrogen, % wt. hydrogen found: 61.55% by weight carbon, 8.31 % wt. hydrogen 6.49% by weight smells.

Bacteriostatic and fungistatic efficacy was on the microorganisms Staphylococcus aureus, Staphyloooccus epidermidis, Bacillus subtilis 10 ug.ml ^-1 , on Escherichia coli, Candida albicans, Saccharomyces cerevisiae, Trichophyton terrestre and Epidermaphyton 100 ug.ml ^-1 .

Example 7

The procedure is as in Example 1 except that the reaction temperature is 50°C and the reaction time is 3 hours. The yield is 85%, i.e. 3.23 g of 2-phenyl-3-dodecyl-5-chloromethyloxazolidine N-oxide.

The invention can find wide application in detergent compositions, in washing and simultaneous disinfection of rooms, tools and in washing textiles. In these compositions, the N-oxides of 2-(monosubstituted phenyl)-3-dodecyl-5-chloromethyloxazolidines would act as bactericidal and fungicidal components.

Claims (2)

5: 247581 calculated: 63.46 3.37 wt. % wt. % carbon, 8.41 wt. hydrogen, nitrogen. found: 63.39 wt. % carbon, 8.50 wt. % hydrogen, 3.32 wt. nitrogen. The bacteriostatic and fungistatic activity was on Staphyloooocus aureus, Staphylococcus epidermidis 10 / Ug-ml on Bacillus subtilis, Trichophyton terrestre, Candidaalbicans and Epidermaphyton 100 µg.ml-1. Example 6 The procedure of Example 1 was followed except that 4.1 g of 2- (2-nitrophenyl) -3-dodecyl-5-chloromethyloxazolidine was used. The yield was 93.8 t 4.00 g of 2- (2-nitrophenyl) -3-dodecyl-5-chloromethyloxazolidine N-oxide. In the infrared spectrum, these determining absorption bands were: 2850, 1580, 1475, 1380, 1120, 1088, 955, 880 cm -1, the following peaks were found in the mass spectrum: 293, 291, 287,285, 273, 271, 257, 255, 197 106, 104. Elemental analysis for C22H35N2O4Cl, molecular weight 426.5% calculated: 61.90% by mass. 6.57 wt. of carbon, 8.21 nitrogen, wt. % hydrogen: 61.55 wt. % carbon, 8.31 wt. 6,49 wt. nitrogen. The bacteriostatic and fungistatic activity was on the microorganisms Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis 10 µg.ml-1, on Escherichia coli, Candidaalbicans, Saccharomyces cerevisiae, Trichophyton terrestre and Epidermaphyton 100 µg.ml-1. Example 7 The procedure of Example 1 was followed except that the reaction temperature was 50 ° C and the reaction time was 3 hours. The yield was 85%, i.e. 3.23 g of 2-phenyl-3-dodecyl-5-chloromethyloxazolidine N-oxide. The invention can find wide application in detergent compositions, as well as in current disinfection! rooms, tools and fabric washing. In these compositions, the N-oxides of 2- (monosubstituted phenyl) -3-dodecyl-5-chloromethyloxazolidines will act as a bacterial and fungicidal component. OUT 1. N-oxides of 2- / monosubstituted phenyl / 3-dodecyl-5-chloromethyloxazolidines of general formula I / 1 / wherein R represents hydrogen, hydroxy, meoxy, bromo, chloro, η nitroscapane in 2, or 3, or 4 247581 6 2. A process for the preparation of N-oxides of 2- (monosubstituted phenyl) -3-dodecylchloromethyloxazolidine of the general formula (I) according to claim 1, characterized in that 2- / monosubstituted phenyl-3-dodecyl-5-chloromethyl-oxazolidine of formula II Wherein R is hydrogen, hydroxy, methoxy, bromo, chloro and nitro at position 2, or 3, or 4, is treated with an aqueous solution of hydrogen peroxide in ethanol at 50 to 60 ° C. 1