CS205170B1 - 5-trimethylammonium salts of 2-furanecarbaldehyde and method of their preparation - Google Patents

Description

The invention relates to 5-trimethylammonium silages of 2-furanecarbaldehyde and to processes for their preparation.

The 5-trimethylammonium salts of 2-furancarbaldehyde have not been described hitherto.

The present invention provides 5-trimethyl-ammonium-furancarbaldehyde formula 2 / CH _3/3

-CH = O χ / ^{7 7} .

wherein X is Cl, Br, or J

According to the invention, the 5-trimethylammonium salts of 2-furancarbaldehyde according to the invention are characterized in that the 5-halo-2-furancarbaldehyde, wherein the halogen is chlorine, bromine or iodine, is reacted with strimethylamine in an organic solvent such as aromatic hydrocarbons. benzene, toluene, chlorobenzene, nitrobenzene in ethers such as diethyl ether, tetrahydrofuran, dioxane, dimethoxyethane, melted in ethyl acetate, acetonitrile, carbon tetrachloride in alcohols such as methanol, ethanol, propanol, isopropanol or mixtures thereof at temperatures between 5 ° C _and 50 ° C 133 to 1330 kPa.

The reaction follows the scheme:

CQ-CH-O (CH _{3) 3} W (+) a) |

CH = 0 r (r) where X = C1, Br, I.

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The compounds according to the invention can also be prepared by the method comprising reacting 5-dimethylamino-2-furancarbaldehyde with methyl chloride, methyl bromide or methyl iodide in an organic solvent such as aromatic hydrocarbons e.g. benzene, toluene, chlorobenzene, nitrobenzene in ethers such as diethyl ether, tetrahydrofuran, dioxane, dimethoxyethane, in alcohols such as methanol, ethanol, propanol, isopropanol, further in ethyl acetate, acetonitrile, carbon disulfide, dimethylformamide, dimethylsulfoxide or mixtures thereof 200 ° C and a pressure of 133 to 1330 kPa.

The reaction proceeds according to the scheme:

(*) / \))

CH-O + ^CH 3 ' ^x - ^(CH 3 ⁾ 3 ^NH 3 | rCH «0 '

wherein X-CH, Br, I

An advantage of the methods of preparation according to the invention is, inter alia, that the syntheses are one-stage and the products obtained are in high yields and high purity. The quaternary ammonium group on the aromatic nucleus is an excellent leaving group and, due to its flax character, allows good water solubility and gives great hope in synthetic and industrial practice for the preparation of water-soluble azomethine-like antibacterials, 2-vinyl, 2-ethyl-5- quaternary ammonium furan salts which may be used in the form of powder, solution, spray and suspensions. The quaternary derivatives have a muscle relaxant effect and thus the muscle relaxant effect.

The following examples illustrate the invention.

EXAMPLE 1 1.6 g (0.01 mol) of 5-bromo-2-furaldehyde (perfectly pure and devoid of HBr) is dissolved in 100 ml of ether and 1.5 g of trimethylamine are introduced into the mixture thus prepared at 3 ° C. After closing the reaction mixture in the absence of light, it is stirred for 48 hours. The luminous crystalline material precipitated to give 1.55g (75%) of 5-trimethylammonium bromide -2-furaldehyde, m.p. 130-145 ° C (decomposition) (methanol, ether)

Example 2

16 g (0.01 mol) of 5-bromofuraldehyde is dissolved in 100 ml of methanol and, with vigorous stirring, poured 20 g of trimethylamine in 50 ml of methanol and heated to 30-50 ° C in an autoclave for 10 hours. After filtering off the crystalline compound, 16.6 g of 70% 2-furaldehyde 5-trimethylammonium bromide were obtained.

Example 3

13 g (0.01 mol) of 5-chlorofuraldehyde is dissolved in 100 ml of dimethoxyethane and, with vigorous stirring, poured 20 g of trimethylamine in 10 ml of benzene and heated to 40 ° C in an autoclave for 1 hour. After filtering off the crystalline material, 15g (80%) of 5-trimethylammonium chloride-2-furaldehyde was obtained.

Example 4 1.55 g (0.01 mol) of 5-dimethylamino-2-fural is dissolved in 30 ml of tetrahydrofuran and 15 g of methyl iodide are added with vigorous stirring. After sealing, the vessel was allowed to warm to 40 ° C and held at this temperature for 48 hours. 1.4 g (50%) of 5-trimethylammonium iodide of 2-furaldehyde are discarded.

Example 5

15.5 g (0.01 mol) of 5-dimethylamino-2-fural and 50 g of methyl iodide and 10 ml of dimethoxyethane are refluxed for 5 hours. The precipitated crystalline material was filtered off and washed with ether. 21g of 5-trimethylmmonium iodide-2-furaldehyde of m.p. 144-157 ° C (75).

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5-trimethylammonium halide-2-fural are compounds of formula (+), O (-) / OTg / ₃ N- / y-CH = OX where X = Cl, Br, I

In summary, the formulas of the compounds C 8 H 11 NO 3 Br; CgH ₂ CINO ₂ £ Cg h ₁₂ ino ₂

Molecular Weight: 234,1 189,5 281,1

Melting points

130-145 C

130-140 C

The structure of the 5-trimethylammonium halides-2-fural according to the invention has been shown by 1 H NMR spectroscopy and ΐΰ spectroscopy.

The 1 H NMR spectrum was measured on a Tsla BS spectrometer in deuterio dimethylsulfoxide using

internal standard of tatratylsilane. The spectrum shows these characteristic bands 1 H NMR IR (CO) (cm For C ₈ H ₁₂ CINO ₂ 9.65 ppm 7.68 ppm 7.28 PPm 1688-1690 C ₈ ^H i ₂ BrNO ₂ 9.69 ppm 7.68 ppm 7.28 PPm 1687-1690 c ₈ h ₁₂ ino ₂ 9.67 ppm 7.69 ppm 7.29 ppm 1687 _T 1690

The iC spectra were measured on a UR-20 spectrophotometer by Zeise Jena KBr.

Claims (3)

OBJECT OF THE INVENTION 1 5-Trimethylammonium salts of 2-furanecarbaldehyde of the formula wherein X = Cl.Br.I (+) (CHgJgN • CH + 0 (-) X 2 A process for the preparation of 5-trimethylammonium salts of 2-furancarbaldehyde according to item 1, characterized in that. the 5-halo-2-furancarbaldehyde formula ^{χ Ά α = 0} X = Cl, Br, I, are reacted with trimethylamine in an organic solvent such as aromatic hydrocarbons, e.g. benzene, toloene, chlorobenzene, nitrobenzene in ethers such as diethyl ether, tetrahydrofuran, diovan, dimethoxyethane in alcohols such as methanol, ethanol, propanol, isopropanol, further in ethyl acetate, acetonitrile, carbon disulphide or mixtures thereof at temperatures ranging from 5 to 50 ° C and pressure 133 to 1330 kPa. 3 process to prepare 5-trimethyl-ammonium-2-furancarbaldehyde according to the claim 1 characterized in that the 5-dimetylaminofural formula 'W 2 ^m - j ^ch £ - ° is treated with methyl chloride, methyl iodide or resp.metylbromidom in an organic solvent such as aromatic hydrocarbons e.g. benzene, toluene, chlorobenzene, nitrobenzene in ethers such as diethyl ether, tetrahydrofurene, dioxane, dimethoxyethane in alcohols such as methanol, ethanol, propanol, isopropanol in styrene acetate, acetonitrile, carbon disulphide, dimethylformamide, dimethylsulfoxide or dimethylsulfoxide in their mixtures ° C and a pressure of 133 to 1330 kP _a .