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

Abstract

The aim of the solution is to prepare new improved ones disinfectants. That purpose is achieved by N-oxides 2- / monosubstituted phenyl-3-dodecyl-5-chloromethyl-oxazolidines of formula I wherein R is hydrogen, hydroxy, methoxy, bromo, chloro, and nitro in position 2, or 3, or 4. purpose the compounds being that it is 2- / monosubstituted phenyl / 3-dodecyl-5-methanesulfonyloxymethyl with an aqueous peroxide solution hydrogen at 50-60 ° C. N-oxides 2-methanesubstituted phenyl-3-dodecyl-5-chlórmety1- oxazolidines and the method of their preparation has utility in detergent compositions, in washing a current disinfection of rooms, tools and washing fabric.

Description

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

The aim of the solution is to prepare new improved disinfectants. This is achieved by the N-oxides of 2- (monosubstituted phenyl) -3-dodecyl-5-chloromethyloxazolidines of formula I wherein R is hydrogen, hydroxy, methoxy, bromo, chloro, and nitro in the 2 or 3 position or 4. This is accomplished by a process for the preparation of these compounds which is treated with 2- (monosubstituted phenyl) -3-dodecyl-5-chloromethyloxazolidine with an aqueous solution of hydrogen peroxide at 50-60 ° C. The N-oxides of 2-monosubstituted phenyl-3-dodecyl-5-chloromethyloxazolidines and a process for their preparation are used in detergent compositions, in the washing and at the same time disinfecting rooms, instruments and in the washing of textiles.

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

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

A. Keith, W. Snipes: Antimicrob. Agents Chemother. 63 (1980)], which was active against Herpes simplex.

4,4-Dimethyloxazolidine derivatives were active against influenza viruses. H. Hunsucker: Chem. Abstr. 89, 141895 (1978)]. Bactericidal activity was found with 3-alkyloxazolidines [e. Boerner, Η. N. Stracke, V. Wehle, Chem. Abstr. 89, 16U923q (1978) by H. Schnegelberger,

H. Bellinger, Chem. Abstr. 80, 52284 (1974); Bansemir K., Bellinger H., Disch K.: Chem. Abstr. 92, 215428 (1980)], 2-piperonyloxazolidines [p. I. Sadych, A. B. Aliev, R. M. Mustafaev: Azerb. Chim. Z. 56 (1972)], 3-alkyl-4-hydroxymethyl-4-methyloxazolidines. Jarcho: Chem. Abstr. 58, 166772b (1983)] and others. Among the fungicidal derivatives of oxazolidine, mention may be made of 2-phenyl-3-cyclooctyloxazolidine |] by BASF A. G .: Chem. Abstr. 58, 4582 (1963)].

However, these derivatives had the disadvantage that they were insoluble in water, limiting their use. Binding of the quaternary ammonium group to the oxazolidine skeleton increased the solubility of these compounds in water, but also reduced their biocidal activity. A disadvantage of these quaternary ammonium salts is that they cannot be mixed with most commercially available surfactants.

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

HjC, ° rl

Η ₃ ε (εΗ ₂ ) _1Ί Νchch ₂ ci

(1) wherein R is hydrogen, hydroxy, methoxy, bromo, chloro and nitro in the 2 or 3 or 4 position. The present invention further provides a process for the preparation of compounds of formula (I) which comprises: 2- (monosubstituted) phenyl 3-dodecyl-5-chloromethyloxazolidine of formula II

wherein R is hydrogen, hydroxy, methoxy, bromo, chloro and nitro in the 2, or 3, or 4 position, is treated with an aqueous solution of hydrogen peroxide in ethanol at 50 to 60 ° C.

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

Example 1

2.65 g (0.01 mol) of 2-phenyl-3-dodecyl-5-chloromethyloxazolidine are added to 20 ml of ethanol. After dissolution of the oxazolidine, 20 ml of 30 wt. aqueous hydrogen peroxide solution. The reaction mixture was heated at 60 ° C under reflux for 2 hours. It is then allowed to stand at 20 to 30 ° C for 10 hours. After completion of the reaction, 0.05 g of platinum oxide is added to quench excess hydrogen peroxide. The mixture is stirred on an electromagnetic stirrer for 24 hours and the platinum oxide is filtered off (after washing with ethanol and dried can be reused).

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

The aqueous layer was azeotropically distilled off at 50 psi (40 kPa) at 40 ° C after addition of an additional 10 mL of butanol. A yield of 92% was achieved, i. 3.5 g of 2-phenyl-3-dodecyl-5-chloromethyloxazolidine N-oxide, which is a non-distillate pale yellow oil. In aqueous solutions it is stable at pH 7 above 30 ° C.

On the infrared spectrum, the following determining absorption bands were: 2920, 2855, 1590, 1470, 1170, 1126 and 960 cm h in the mass spectrum: 293, 291, 242, 240, 228, 226, 197, 106, 104.

Elemental analysis for C ₃₆ H _{2 N 2} Cl NO Molecular Weight 381.5

calculated: 69.20% wt. % carbon, 9.44 wt. nitrogen, H 3Γ67% wt. found: 69,08% wt. % carbon, 9.49 wt. H 3.63% wt. nitrogen.

The 2-phenyl-3-dodecyl-5-chloromethyloxazolidine N-oxide had bacteriostatic and fungistatic activity on Staphylococcus aureus, Staphylococcus epidermidis lyug.ml ^-1 , Bactllus substilis, Streptococcus faecalis, Microsporum gypsa and Microsporum gypsa. ml per microorganism Escherichia coli, Shigella flexneri, Candida, albicans and Saccharomyces cerevisiae 100 µg.ml ^-1 .

Example 2

The procedure was as in Example 1 except that 2.81 g of 2- (2-hydroxyphenyl) -3-dodecyl-5-chloromethyloxazolidine was used. The yield was 86.8%, ie. 3.45 g of 2- (2-hydroxyphenyl) -3-dodecyl-5-chloromethyloxazolidine N-oxide.

On the infrared spectrum, the following determining absorption bands hurt: 2930, 2860, 1590, 1470, 1210, 1120, 1098, 965 cm ^-1 . The following peaks were determined in the mass spectrum: 293, 291, 258, 256, 244, 242, 197, 106, 104.

Elemental analysis for C ₂₁ H ₁₆ O ₄ Cl ₃ , MW 397.5

calculated: 66.42% by weight, 3.52% by weight, . atoms, . nitrogen 9, U6 wt. hydrogen. found: . 66,05% by weight, . atoms. 9, 17 wt. H, 3., 48 masses, . nitrogen. - - Baktoriostatioká and £ ungí-etatický úctnost was on microorganisms Staphylococcus aureus ..

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

and Epidermaphyton luu '

Example 3

The procedure was as in Example 1 except that 3.96 g of 2- (4-methoxyphenyl) -3-dodecyl-5-chloromethyl-oxazolidine was used. The yield was 94.8%, ie. 3.90 g of 2- (4-methoxyphenyl) -3-dodecyl-5-chloromethyl-oxazolidine N-oxide.

On the infrared spectrum, these were the determining ab bands: 2850, 1585, 1470, 1260, 1100, 1095, 1045, 965 om ^-1 . In the mass spectrum the following peaks were determined: 293, 291, 272 ', 270, 258, 256, 197, 106, 104.

Elemental analysis for ^C 23 ^H 38 ^NO 3 ^{Cl 1} Molecular Weight 411.5 Calculated: 67.07% wt. % of carbon, 9.23 wt. H,

3.40% wt. % nitrogen found: 66.94 wt. % of carbon, 9.36 wt. H,

3.36% wt. nitrogen.

Bacteriostatic and fungistatic activity on Staphylococcus aureus, Staphylococcus epidermidis, Streptooocous faecalis and Baclllus subtilis was 10 µg.ml, on Candlda albicans and Epidermaphyton 100 µg.ml ^-1 .

Example 4

The procedure was as in Example 1 except that 4.44 g of 2- (3-bromophenyl) -3-dodecyl-5-chloromethyloxazolidine was used. The yield was 92.3%. 4.25 g of 2- (3-bromophenyl) -3-dodeoyl-5-chloromethyl-oxazolidine N-oxide.

On the infrared spectrum, the following absorption bands were determined: 2850, 1580, 1470, 1105, 1090, 960, 580 cm ⁴ . the mass spectra were as follows: 382, 380, 321, 319, 307, 305, 293, 291, 289, 197, 106, 104.

Elemental analysis for ^C 22 ^H 35 ^NO 2 ^BrCl · Molecular weight 460.5 Calculated: 57.33% wt. % of carbon, 7.60 wt. H,

3.04 wt. found: 57.00 wt. % of carbon, 7.82 wt. H,

2.97% wt. nitrogen.

Bacteriostatic and fungistatic efficacy was on Staphylococous aureus, Staphylococous epidermidis, Trichophyton terrestre, Candida albicans and Epidermaafcyton 100 / µg-ml.

Example 5

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

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

Elemental analysis for C ₂₂ H ₃₃ NO ₂ Cl ₂ , MW 416 i

calculated: 63.46 3.37 % wt. % wt. % of carbon, 8.41 wt. hydrogen, nitrogen. found: 63.39 % wt. alkyl, 8.50 % wt. H, 3.32 % wt. nitrogen.

The bacteriostatic and fungistatic efficacy was on Staphylococcus aureus, Staphylococcus epidermidis 10 / Ug-ml ¹ , Bacillus subtilis, Trichophyton terrestre, Candida albicans and Epidermaphyton 100 µg.ml ^-1 .

Example 6

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

On infrared! spectra were as follows: 2850, 1580, 1475, 1380, 1120, 1088, 955, 880 cm ^{@ -1} . The following peaks were determined 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, MW 426.5 *

calculated: 61.90 wt. 6.57% wt. carbon, 8.21 nitrogen, % wt. H found: 61.55% wt. carbon, 8.31 % wt. H 6.49% wt. nitric acid.

Bacteriostatic and fungistatic efficacy was on Staphylococcus aureus, Staphyloooccus epidermidis, Bacillus subtilis 10 µg.ml ^-1 , Escherichia coli, Candida albicans, Saccharomyces cerevisiae, Trichophyton terrestre and Epidermaphyton 100 µg.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 was 85%. 3.23 g of 2-phenyl-3-dodecyl-5-chloromethyl-oxazolidine N-oxide.

The invention can find wide application in detergent compositions, in washing and at the same time disinfecting! rooms, tools and textiles. In these compositions, the N-oxides of 2- (monosubstituted phenyl) -3-dodecyl-5-chloromethyloxazolidines would act as a bactericidal and fungicidal component.

Claims (2)

OBJECT OF THE INVENTION N-oxides of 2- (monosubstituted phenyl) -3-dodecyl-5-chloromethyloxazolidines of the general formula I (1) wherein R represents hydrogen, hydroxy, methoxy, bromine, chlorine, η nitroscopylene 2, or 3, or 4. 2. A process for the preparation of the N-oxides of 2- (monosubstituted phenyl) -3-dodecyl-chloromethyloxazolidines of the formula I according to claim 1, characterized in that to 2- (monosubstituted phenyl) -3-dodeoyl-5-chloromethyloxazolidines of the formula II (11) wherein R is hydrogen, hydroxy, methoxy, bromo, chloro and nitro in the 2, or 3, or 4 position, is treated with an aqueous solution of hydrogen peroxide in ethanol at 50 to 60 ° C.