Cyclo-bis[(1z)-1-imino-2-methyl-1h-inden-3-yl-1,2,4-thiadiazole-3,5-diamine], possessing property of acid dye for silk, wool and polyamide 6

FIELD: chemistry.

SUBSTANCE: invention relates to novel heterocyclic compound, representing cyclo-bis[(1Z)-1-imino -2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine]

EFFECT: compound as acid dye for silk, wool and polyamide 6.

3 dwg, 5 ex

 

Introduction

The invention relates to the chemical industry, namely, to receive a new heterocyclic compounds that can be used as an acid dye.

The level of technology

It is known connection (Berezin, R., Vorobyov, Y., Smirnov, R. P. Synthesis and study of heterocyclic compounds based on 1,3-indandion // Joh. 1998. So 68. Vol.6. S. 1018-1020), a structural analogue of the claimed compounds.

However, it does not possess the property of acid dye.

Known compounds (Berezin, R., Y. Vorobyev, Synthesis and properties of macroheterocyclic compounds with fragments substituted benzidine // Joh. 2006. So 76. Vol.8. S. 1369-1374).

They don't have coloring properties and, therefore, cannot be used for dyeing in the solutions.

Known isocratically (Borodkin C. F. Chemistry of dyes. - M.: Chemistry, 1981. S. 95, 97), which dye protein fibers, but not dyed nylon, for example:

Dyes based on 2-amino-5-mercapto-1,3,4-thiadiazole (1. Shukurov n, Kukayev M. A. a New method of synthesis of 2-amino-5-alkyl(aralkyl)thio-1,3,4-thiadiazolo // Zhur.org.chem.. 1993. So 29. Vol.11. S. 2327; 2. Hani R., Varadiya. Disperse dyes based on 2-amino-5-mercapto-1,3,4-thiadiazolo / CHC. 2009. No. 10. S. 1558-1563) paint only polyamide fibers in red and pink shades, for example:

Copper-containing active vinylsulfonate dyes blue (Patent RF №2047630. Publ. 10.11.1995) paint cellulose, natural and synthetic polyamide fibers:

The invention

Inventive task was to find a new macroheterocyclic compounds that can be used as acid dyes for silk, wool and nylon.

The problem is solved macroheterocyclic compound cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine] formula

The structure of this compound proved by data of elemental analysis, IR, electronic and NMR1N spectroscopy.

In the IR spectra of the claimed compounds (Fig.1) you can allocate a number of common absorption bands with similar (Berezin, R., Vorobyov, Y., Smirnov, R. P. Synthesis and study of heterocyclic compounds based on 1,3-indandion // Joh. 1998. So 68. Vol.6. S. 1018-1020).

In the electronic spectra of cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine] observed an intense absorption at 465 nm (lgε 4.65) and less intense - at 340 nm, recorded in water (Fig.2). The character of the spectrum shows closedeye exists in solution predominantly in the form of a monomer.

In NMR spectra1H there is a singlet in the region of 1.8 M. D. (1:1), which characterizes the presence of a methyl group and a multiplet in the region of 7.6-8 M. D. (1:1,5), which indicates the presence of phenyl substituents in the coordination cavity of the molecule and the presence of benzene fragments in the connection. Methyl group out of the plane of the macrocycle and are located on the phenyl rings, so they get their ring current, and therefore the peak is shifted to the right on the scale (3→1.8 m doctor of medicine) (Fig.3).

Cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine] is a substance of bright red color, having a solubility in water, DMF, H2SO4, chloroform, ethanol.

The proposed new connection has the property of acid dye and can be used for dyeing silk, wool and nylon.

Information confirming the possibility of carrying out the invention

To obtain the target product using the following ingredients:

diethylphthalate GOST 8981-78,

xylene THE 2631-018-781 19972-06,

sodium metal THAT 6-09-356-77,

ethyl ester propionic acid GOST 22300-76,

glacial acetic acid GOST 18870-72,

ammonium acetate GOST 3 1 17-78,

ethanol GOST 18300-72,

hydrochloric acid GOST 14261-77,

the hydrogen peroxide GOST 10929-76,

dicyandiamide TU 6-09-16-919-75,

caustic soda GOST 4328-77.

Appl is radiated compound obtained in the following way: first synthesize Diemen 2-methylindoline interaction diethylphthalate, metallic sodium, ethyl ester propionic acid, ammonium acetate and glacial acetic acid, followed by the interaction of the compounds with 3,5-diamino-1,2,4-thiadiazole in the ratio 2:2 with the circuit in the loop.

Example 1. The synthesis of the target product.

In a three-neck flask, equipped with reflux condenser, thermometer and stirrer, made of 20 ml of xylene and 10 g of sodium metal, is heated under stirring (100°C) for 1 hour, get a whitish-gray suspension, then the suspension is cooled to 50°C and gradually poured a mixture of 50 ml of diethylphthalate and 70 ml of ethyl ether propionic acid. Stirred for 2 hours, formed dark red thick mass. Krasnoarmeisky aqueous solution of Na-connection discolor concentrated hydrochloric acid, the precipitate is filtered and washed with ethyl alcohol. Yield: 78%, tPL=84-85°C. Then, 15 g dissolved in 50 ml of glacial acetic acid and gradually add 70 g of ammonium acetate. The mixture is boiled for 3 hours, cooled and leave for days, then filtered, the precipitate washed with water and dried. Output diimine 2-methylindoline 75%. The red substance in the powder, so pl. 178°C. Found, %: C, 74.5; H, 6.37; N, 16.8. C10H10N2. Calculated, %: C, 75.95; H, 6.33; N, 17.72.

In a round-bottom three-neck flask with a capacity of 500 ml, equipped with the reverse was built in the ICOM, a nozzle for passing hydrogen sulfide, was placed a solution of dicyandiamide 42 g (0.5 mol) in 200 ml of water and incubated at 75°C for 12 hours, then passed through a solution of hydrogen sulfide for 30 hours. The yellow liquid is cooled to 45°C and add 15 ml of 40% sodium hydroxide solution, filtered, the filtrate was kept at 0°C for 24 hours. Sediment in the form of prismatic blades filtered and washed with ice water (60 ml). The output amidinothiourea 35.4 g (60%), so different. 170-172°C. Found, %: C 19.98; H, 5.06; N 47.2; S 26.95. C2H6N4S. Calculated, %: C 20.35; H 5.08; N 47.45; S 27.12. Into a flask equipped with reflux condenser and stirrer, contribute 11.8 g (0.1 mol) of amidinothiourea and 250 ml of ethanol, add 10 ml (0.1 mol) of concentrated hydrochloric acid and brought to a boil, then bring in a solution of 170 ml (0.3 mol) of 20% hydrogen peroxide. Precipitated sulfur is filtered and cooled filtrate falls 3,5-diamino-1,2,4-thiadiazole. The output of 7.67 g (66%), so pl. 169-171°C. Found, %: C 21.41; H, 3.38; N 43.47; S 26.41. C2H4N4S. Calculated, %: C 20.69; H, 3.45; N 48.28; S 27.58.

Into a flask equipped with reflux condenser and stirrer, make 0.49 g (3.5 mmole) diimine 2-methylindoline, 0.36 g (3.1 mmole) of 3,5-diamino-1,2,4-thiadiazole and 7 ml of glacial acetic acid. The mixture is boiled for 3 hours. Upon completion of the reaction the solution is cooled, poured in a minimum amount of water and it is ruleswhat weak alkali solution. The resulting product is filtered and washed on the filter with acetone. Dried at 100°C.

Output cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine]: 0.47 g (58%). The substance of a bright red powder, soluble in water, DMF, H2SO4, chloroform, ethanol, so start decomp. 200°C.

IR spectrum, ν, cm-1: (C=C) 1609; (C-C) 1153; (C=N) 1115; (N-H) 3422; (C-N) 1271; (C-S) 630; δ (C-H) 840.

ESP in the water, λmaxnm: 340, 465 nm (Igε 4.65) (Fig.1). ESP in the water, λmaxnm: 340, 465 nm (lgε 4.65) (Fig.2). An NMR spectrum1H, δ, M. D.: 1.8 W; 7,6-8 m (4 protons) (Fig.3).

Found, %: C, 55.85; H, 4.37; N 22.54; S 11.95. C24H16N8S2.

Calculated, %: C 60; H, 3.34; N 23.33; S 13.33.

Example 2. The use of cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine] as the acid dye for silk. Dyeing conducted according to the methodology (Laboratory workshop on the application of dyes // Ed. by B. Melnikov N. - M.: Chemistry. 1972. C. 7-14).

A sample of silk fibers weighing 1 g is placed in a dye bath composition (g/l):

Cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine]6
Glauber's salt40
Module baths50

Within 15-30 minutes heat the van is at 60°C and kept at this temperature for 40 minutes and 20 minutes in the cooling up to 30°C bath.

The sample was then drained, washed thoroughly with warm, then cold water and treated with a solution of sulfuric acid composition (ml):

sulfuric acid1
water50

The sample is drained, washed thoroughly with warm, then cold water, and dried.

Example 3. The use of cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine] as the acid dye for wool. Dyeing conducted according to the methodology (Laboratory workshop on the application of dyes // Ed. by B. Melnikov N. - M.: Chemistry. 1972. C. 7-9).

A sample of wool weighing 1 g is placed in a dye bath composition (g/l):

Cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine]6
Glauber's salt40
Module baths50

Within 15-30 minutes heat the bath to 60°C and kept at this temperature for 40 minutes and 20 minutes in the cooling up to 30°C bath.

The sample was then drained, washed thoroughly with warm, then cold water and treated with a solution of sulfuric acid composition is a (ml):

sulfuric acid1
water50

The sample is drained, washed thoroughly with warm, then cold water, and dried.

Example 4. The use of cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine] as acid dyes for nylon. Dyeing conducted according to the methodology [Laboratory workshop on the application of dyes // Ed. by B. Melnikov N. - M.: Chemistry. 1972. C. 7-14).

The sample fiber nylon weighing 1 g is placed in a dye bath composition (g/l):

Cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine]6
Glauber's salt40
Module baths50

Within 15-30 minutes heat the bath to 60°C and kept at this temperature for 40 minutes and 20 minutes in the cooling up to 30°C bath.

The sample was then drained, washed thoroughly with warm, then cold water, and treated with a solution of sulfuric acid composition (ml):

sulfuric acid1
water50

The sample is drained, washed thoroughly with warm, then cold water, and dried.

Example 5. The use of cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine] as the acid dye for silk, wool and nylon. Dyeing of all samples was performed from one bath.

Samples of the fibers of wool, silk and nylon in the ratio of 1:1:1 weight of 1 g is placed in a dye bath composition (g/l):

Cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine]6
Glauber's salt40
Module baths50

Within 15-30 minutes heat the bath to 60°C and kept at this temperature for 40 minutes and 20 minutes in the cooling up to 30°C bath.

Then the samples are drained, washed thoroughly with warm, then cold water and treated with a solution of sulfuric acid composition (ml):

sulfuric acid1
water50

Samples drained, washed thoroughly with warm, then cold water, and dried.

brassy color charts according to the examples 2, 3, 4, 5 are attached.

Cyclo-bis[(1Z)-1-imino-2-methyl-1H-inden-3-yl-1,2,4-thiadiazole-3,5-diamine]
,
having the property of acid dye for silk, wool and nylon.



 

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39 cl, 3 tbl, 25 ex

FIELD: organic chemistry, pharmaceutical composition.

SUBSTANCE: new isoindoline-1-on-glucokinase activators of general formula I , as well as pharmaceutically acceptable salts or N-oxide thereof are disclosed. In formula A is phenyl optionally substituted with one or two halogen or one (law alkyl)sulfonyl group, or nitro group; R1 is C3-C9cycloalkyl; R2 is optionally monosubstituted five- or six-membered heterocyclic ring bonded via carbon atom in cycle to amino group, wherein five- or six-membered heteroaromatic ring contains one or two heteroatoms selected form sulfur, oxygen or nitrogen, one of which is nitrogen atom adjacent to carbon atom bonded to said amino group; said cycle is monocyclic or condensed with phenyl via two carbon atoms in cycle; said monosubstituted with halogen or law alkyl heteroaromatic ring has monosubstituted carbon atom in cycle which in not adjacent to carbon atom bonded to amino group; * is asymmetric carbon atom. Claimed compounds have glucokinase inhibitor activity and useful in pharmaceutical composition for treatment of type II diabetes.

EFFECT: new isoindoline-1-on-glucokinase activators useful in treatment of type II diabetes.

23 cl, 3 dwg, 43 ex

FIELD: pharmaceutical industry, medicine.

SUBSTANCE: invention relates to 5-membered N-heterocyclic compounds and salts thereof having hypoglycemic and hypolipidemic activity of general formula I , wherein R1 is optionally substituted C1-C8-alkyl, optionally substituted C6-C14-aryl or optionally substituted 5-7-membered heterocyclic group, containing in ring 1-4 heteroatoms selected from oxygen, sulfur and nitrogen; or condensed heterocyclic group obtained by condensation of 5-7-membered monoheterocyclic group with 6-membered ring containing 1-2 nitrogen atoms, benzene ring, or 5-membered ring containing one sulfur atom; { is direct bond or -NR6-, wherein R6 is hydrogen atom or C1-C6-alkyl; m = 0-3, integer; Y is oxygen, -SO-, -SO2- or -NHCO-; A ring is benzene ring, condensed C9-C14-aromatic hydrocarbon ring or 5-6-membered aromatic heterocyclic ring containing 1-3 heteroatoms selected from oxygen and nitrogen, each is optionally substituted with 1-3 substituents selected from C7-C10-aralkyloxy; hydroxyl and C1-C4-alkoxy; n = 1-8, integer; B ring is nitrogen-containing 5-membered heterocycle optionally substituted with C1-C4-alkyl; X1 is bond, oxygen or -O-SO2-; R2 is hydrogen atom, C1-C8-alkyl, C7-C13-aralkyl or C6-C14-aryl or 5-6-membered heterocyclic group containing in ring 1-3 heteroatoms selected from oxygen, sulfur and nitrogen, optionally substituted with 1-3 substituents; W is bond, C1-C20-alkylene or C1-C20-alkenylene; R3 is -OR8 (R8 is hydrogen or C1-C4-alkyl) or -NR9R10 (R9 and R10 are independently hydrogen or C1-C4-alkyl). Compounds of present invention are useful in treatment of diabetes mellitus, hyperlipidemia, reduced glucose tolerance, and controlling of retinoid-associated receptor.

EFFECT: new medicines for treatment of diabetes mellitus, hyperlipidemia, etc.

26 cl, 518 ex, 3 tbl

FIELD: organic chemistry.

SUBSTANCE: method relates to new method for production of 5-chloro-4-[(2-imidazoline-2-yl)amino]-2,1,3-benzothiadiazole hydrochloride of formula I . Claimed compound is high effective drug and is used in medicine as myorelaxant of central action. Claimed method includes condensation of N,N-dimethyldichloromethyleneammonium chloride with 5-chloro-4-amino-1,1,3-benzothiadiazole in organic solvent followed by treatment of formed alpha-chloroformamidine of formula R-N=C(Cl)N(CH3)2, wherein R is 5-chloro-2,1,3-benzothiazol-4-yl, with ethylenediamine. Formed intermediate of formula R-N=C(NH-CH2-CH2-NH2)N(CH3)2 is treated with hydrochloric acid, heated in organic solvent and 5-chloro-4-[(2-imidazoline-2-yl)amino]-2,1,3-benzothiadiazole hydrochloride of formula I is isolated.

EFFECT: simplified method for preparation of target compound directly in hydrochloride form.

FIELD: organic chemistry, chemical technology, agriculture.

SUBSTANCE: invention describes substituted azadioxocycloalkenes of the general formula (I): wherein A means unsubstituted or methyl-substituted dimethylene; Ar means unsubstituted or fluorine-substituted ortho-phenylene, thiophendiyl or pyridindiyl; E means group of the formula: wherein G means oxygen atom, groups -O-CH2-, -CH2-O- or -C(CH3)=N-O-CH2-; Z means unsubstituted or substituted phenyl, pyrimidinyl or thiadiazolyl, or naphthyl. Invention describes 4 methods for preparing compounds of the formula (I), 5 species of intermediate compounds used for preparing compounds of the formula (I), fungicide agents comprising compound of the formula (I) as an active substance, a method for preparing fungicide agents, method for control of harmful fungi using compound of the formula (I). Compounds of the formula (I) show fungicide properties and therefore they can be used in agriculture.

EFFECT: improved preparing methods, valuable properties of compounds.

13 cl, 5 tbl, 18 ex

FIELD: organic chemistry, pesticides, agriculture.

SUBSTANCE: invention relates to compounds that elicit high pesticide activity and can be used in control of pests of domestic and agricultural animals. Indicated compounds show the formula (I):

wherein R1 means halogen atom, (C1-C6)-halogenalkyl; R2 means hydrogen atom (H), (C1-C6)-alkyl, (C1-C6)-alkylene-phenyl; X1 means nitrogen atom (N); X2 means group C(CN); X3 means oxygen atom (O); Q means CH; R3 and R4 mean independently of one another hydrogen atom (H) or in common with carbon atom with which they are bound form (C3-C7)-cycloalkyl ring; R5 means a substitute taken among group including (C1-C6)-halogenalkyl, halogen atom being if m above 1 then substitutes R5 can be similar or different; m = 1, 2 or 3; n = 0 or 1. Also, invention describes a method for their preparing and method for control of pests.

EFFECT: valuable pesticide properties of compounds.

7 cl, 3 tbl, 14 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention relates to biologically active compounds, in particular, to substituted 5R1,6R2-thiadiazine-2-amines and pharmaceutical compositions comprising thereof that can be used in medicine as potential pharmacologically active substances eliciting the unique combination of properties: expressed anticoagulant activity in combination with capacity to inhibit aggregation of platelets. Effect of these substances differ from preparations used in medicinal practice and they can be used therefore in treatment of such diseases as myocardium infarction, disturbance in cerebral circulation, rejection of transplanted organs and tissues and so on. Indicated compounds correspond to the formula (I):

wherein values of radicals R1, R2 and R3 are given in the invention claim.

EFFECT: valuable medicinal properties of compounds.

4 cl, 2 tbl, 7 dwg, 33 ex

FIELD: organic chemistry, chemical technology, medicine.

SUBSTANCE: invention relates to a method for preparing derivatives of indole of the general formula (I):

wherein R1 represents hydroxy-group; R2 represents hydrogen atom, (C1-C6)-alkyl, (C1-C6)-alkoxy-group, (C2-C6)-alkoxyalkyl or 4-methoxybenzyl; R3 represents hydrogen atom or (C1-C6)-alkyl; each among R4 and R represents independently hydrogen atom, (C1-C6)-alkyl or (C1-C6)-alkoxy-group; D represents an ordinary bond, (C1-C6)-alkylene, (C2-C6)-alkenylene or (C1-C6)-oxyalkylene; in the group-G-R6 wherein G represents an ordinary bond, (C1-C6)-alkylene; R represents saturated or unsaturated carbocyclic ring (C3-C15) or 4-15-membered heterocyclic ring comprising 1-5 atoms of nitrogen, sulfur and/or oxygen wherein this ring can be substituted. Also, invention describes a method for preparing derivatives of indole and DP-receptor antagonist comprising derivative of the formula (I) as an active component. As far as compounds of the formula (I) bind with DP-receptors and they are antagonists of DP-receptors then they can be useful for prophylaxis and/or treatment of diseases, for example, allergic diseases.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

11 cl, 7 tbl, 353 ex

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