The way to obtain 1-acetyl-2-imidazolidone
The invention relates to organic chemistry, in particular, to a method for producing 1-acetyl-2-imidazolidone by reacting 2-imidazolidone and acetic anhydride, taken in a molar ratio of 1:2, followed by dilution of the reaction mixture of a lower alkyl acetate, with stirring at 70-75S until a homogeneous leggierissimo suspension, cooling the mass, filtering, washing the resulting product with alkyl acetate and drying. Get a product with mass fractions of the basic substance is not less than 96%, yield 77% and a melting point 190-S (according to literature data, 188-S). The technical result - the simplicity and adaptability of the method, a high product yield while achieving a high degree of purity.
The invention relates to organic chemistry, in particular, to obtain 1-acetyl-2-imidazolidone used in the production of insecticides and medicines.
Was first described way to obtain this product by boiling 2-imidazolidone with excess acetic anhydride. By recrystallization of the selected product from acetonitrile, the compound obtained with a melting point which is 171,5-173, 0mm C. Dan elemental analysis prodazhnyh reagents taken in the amount of 10 mol of acetic anhydride, 1 mol of 2-imidazolidone for 30 min with distillation of the excess acetic anhydride under reduced pressure and recrystallization of the residue from alcohol. The obtained product with a melting point of 176 S (J. C. Roberts, Am. Chem. Soc., 86, 177-178, 1964).
By the described methods receive a product with a low melting point, which may indicate low quality.
The prototype of the proposed method to obtain product is the way, which consists in the interaction of 2-imidazolidone with acetic anhydride, taken in equimolar ratio at 65 degree Celsius for 1 h, then at 90 ° C for 1 h and then cooled mass by filtration of the product and double recrystallization from chloroform. Get a product with so pl. 188-S and yield of 39%. The structure of the product is confirmed by elemental analysis (Belgian patent 626254, a 01 n, 1963).
The disadvantage of this method is the low degree of transformation of the raw product at the specified ratio of the reactants, which leads to the necessary purification of the crude product by recrystallization and low yield of the target compound. In addition, in the process forming a thick supermassively mass, Catania is a simplification of the process, ensuring manufacturability, increase the yield and quality of the target product.
The problem is solved in that the process of interaction of 2-imidazolidone and acetic anhydride is carried out at their molar ratio 1:2, followed by dilution of the reaction mixture of a lower alkyl acetate, stirring the mixture at 70-75S to education leggierissimo suspension, cooling the mass, filtering, washing the resulting product is a lower alkyl acetate and drying.
The proposed method allows to obtain a product with a melting point 190-S.
The following examples illustrate the invention.
Example 1. A mixture of 42.0 g of 2-imidazolidone (0,4683 mol), 97,2 g of acetic anhydride (0,9366 mol), stirred for 1 h at a temperature of 65 degree Celsius and then 1 h at 90. Then add in the weight 42 cm3ethyl acetate and stirred at 70-75S until a homogeneous leggierissimo suspension.
Cool the mass and after exposure is stirred until a homogeneous suspension is then filtered product. Wash the residue with ethyl acetate, squeezed and dried at 100-110S.
Receive a product with a mass fraction of 96%, yield 77% and a melting point 190-192 the om 77,3%, mass fraction of 96% and a melting point 190-S.
Thus, the proposed method differs from the method on the prototype of the simplicity and adaptability of the process, high yield and degree of purity of the product by eliminating the need for purification by recrystallization and the use of toxic solvent.
The way to obtain 1-acetyl-2-imidazolidone the interaction of 2-imidazolidone with acetic anhydride when heated with the release of the product by cooling the reaction mixture, characterized in that the communication process is carried out at a molar ratio of 2-imidazolidone and acetic anhydride 1:2, followed by dilution of the reaction mixture of a lower alkyl acetate, with stirring at 70-75S until a homogeneous leggierissimo suspension, cooling the mass, filtering, washing the resulting product with alkyl acetate and drying.
FIELD: organic chemistry, herbicides, agriculture.
SUBSTANCE: invention relates to new substituted benzoylketones of the general formula (I): , all possible tautomeric forms and possible salts that can represent active substance as a component of herbicide agent. In the formula (I) A means (C1-C4)-alkyl; R1 means cyclo-(C3-C6)-alkyl; R2 means hydrogen atom (H), cyano-group (CN); R3 means hydrogen atom (H), halogen atom, CF3, (C1-C4)-alkylsulfonyl; R4 means halogen atom; X means groups: or wherein R5 means (C1-C4)-alkyl, (C1-C4)-alkoxy-group, (C1-C4)-alkylthio-group, di-(C1-C6-alkyl)-amino-group; R6 means (C1-C4)-alkyl, (C1-C4)-alkoxy-group, cyclo-(C3-C6)-alkyl; n = 0 or 1 including all possible tautomeric forms and possible salts. Compounds of the formula (I) elicit herbicide activity and can be used in herbicide composition.
EFFECT: valuable properties of compounds.
3 cl, 1 sch, 3 tbl, 13 ex
FIELD: organic chemistry.
SUBSTANCE: invention describes novel substituted benzoylcyclohexenones of the general formula (I): wherein values Q, Y, Z, R1-R5 and their possible tautomeric forms and their possible salts given in the invention claim. Invention proposes substituted benzoylcyclohexenones of the general formula (I) that possess the herbicide activity.
EFFECT: valuable property of compounds.
2 cl, 10 tbl, 6 ex
SUBSTANCE: in formula (1) compound, cysteinprotease is cathepsin K, cathepsin S, cathepsin L or cathepsin B. In formula (I) R is , AA1 is a bond, AA2 is a bond, R7 and R8 each independently represents hydrogen, C1-8 alkyl, CycA or C1-8 alkyl, substituted CycA, R9 is hydrogen, values of the rest of the radicals are given in the formula of invention. The invention also relates to a pharmaceutical composition, containing a formula (I) compound as an active ingredient, to a cysteinprotease inhibitor, method of inhibiting cysteinprotease, use of formula (I) compound in obtaining cysteinprotease inhibitor.
EFFECT: compound has inhibitory activity towards cysteinprotease.
10 cl, 16 tbl, 8 dwg, 224 ex
SUBSTANCE: in formula (1) A is a nitrogen atom or CH; when A is a nitrogen atom, B is NR9 (where R9 is a C1-10alkyl group), when A is CH, B is a sulphur atom, R1 is a phenyl group (where the phenyl group is substituted with one or more substitutes selected from a group consisting of halogen atoms, C1-10alkyl group and C1-10alkoxy groups (where C1-10alkyl groups and C1-10alkoxy groups are not substituted of substituted with one or more halogen atoms)); L1 is a bond; X is OH; R2 is a C1-6alkyl group; L2 is a bond; L3 is NH; L4 is a bond or NH; Y is an oxygen atom or sulphur atom; R3 is a thienyl group (where the thienyl group is substituted with CONR29R30 (where R29 is hydrogen or a C1-10alkyl group, and R30 is an amino group (where the amino group is not substituted or substituted with a pyridyl group), mono- or di-C1-10alkylamino group, N-methylpiperzinyl group, piperidine group, morpholine group or C1-10alkyl group (C1-10alkyl group is substituted with one or more substitutes selected from a group consisting of a carboxyl group, carbamoyl groups, pyrroldinyl groups, tetrahydrofuryl groups or morpholine groups) or R29 and R30 together denote -(CH2)m3-G-(CH2)m4- (where G is CR31R32 (where R31 is a hydrogen atom and R32 is a C1-10alkylcarbonylamino group or pyrrolidinyl group) and each of m3 and m4 is independently equal to an integer from 0 to 5 provided that m3+m4 equals 3, 4 or 5), or NR29R30 as a whole denotes a piperidine group or pyrrolidinyl group (where the piperidine group or pyrrolidinyl group is substituted with two substitutes independently selected from a group consisting of: hydroxyl groups and C1-10alkoxy groups) or 2-(4-oxopyrridin-1(4H)-yl)acetyl group), phenyl group (where the phenyl group is substituted with one substitute selected from a group consisting of C1-10alkyl groups, C1-10alkylcarbonyl groups and C1-10alkylaminocarbonyl groups, (where C1-10alkyl group, C1-10alkylcarbonyl group and C1-10alkylaminocarbonyl group are substituted with one or two substitutes selected from a group consisting of hydroxyl groups, carboxyl groups and carbamoyl groups)), phenyl group (where the phenyl group is substituted with one C1-10alkylaminocarbonyl group or one halogen atom), dihydrobenzo[1,4]dioxine group or benzo[1,4]oxazine group. The invention also relates to a medicinal agent containing the disclosed compound as an active ingredient and to a thromopoeitin receptor activator which is a formula (1) compound.
EFFECT: disclosed compounds have thrombopoietin receptor agonist properties.
8 cl, 11 tbl, 128 ex
SUBSTANCE: present invention relates to a method of producing (meth)acrylates of N-hydroxy-alkylated amides, in which cyclic N-hydroxyalkylated amides (C): , where Z1 denotes unsubstituted or mono-substituted nitrogen (N-R3); R1 and R2, in each case independently denote an alkylene with 2-20 carbon atoms, cycloalkylene with 5-12 carbon atoms, arydene with 6-12 carbon atoms; R3 denotes hydrogen, alkyl with 1-18 carbon atoms, alkenyl with 2-18 carbon atoms, aryl with 6-12 carbon atoms or cycloalkyl with 5-12 carbon atoms; etherified with methacrylic acid or reesterified with at least one (meth)acrylic ester (D) in the presence of at least one heterogeneous catalyst selected from a group consisting of inorganic salts (Co), having pKb not higher than 7.0 and not lower than 1.0, and its solubility in the reaction medium at 25°C is not more than 1 g/l, and enzymes (F) selected from a group comprising esterase (E.C.3.1.-.-), lipase (E.C.22.214.171.124), glycosylase (E.C.3.2. -.-) and protease (E.C.3.4. -.-), where the heterogeneous catalyst is separated from the reaction mixture through filtration, electrofiltration, absorption, centrifuging or decantation.
EFFECT: efficient method of producing (meth)acrylates of N-hydroxyalkylated amides.
6 cl, 5 ex
SUBSTANCE: invention refers to new compounds of formula (I) and their pharmaceutically acceptable salts, which inter alia inhibit hepatotropic hepatitis C virus and are applicable in treating hepatitis C virus. In formula (I) R1 is specified in a group consisting of
is specified in a group consisting of a carbon-carbon single bond and carbon-carbon double bond; R5, R6, R11, R12, R13 and R14 are independently specified in a group consisting of a hydrogen atom, methyl and a protective group for nitrogen specified in C1-6alkylsulphonyl; R7 represents a hydrogen atom; R2 is specified in a group consisting of a halogen atom, C1-6alkyl and heterocyclyl specified in 5-merous heteroaryl with 1-2 heteroatoms specified in nitrogen, oxygen and sulphur, wherein alkyl is optionally substituted by one or more substitute optionally specified in a group consisting of a halogen atom; and heterocyclyl is optionally substituted by C1-3alkyl; R3 is specified in a group consisting of C1-6alkyl, C2-4alkenyl, C1-6alkyloxy and a halogen atom; L means a bond, and R4 is specified in a group consisting of C5-C6-carbocyclyl, or R4 means carbocyclyl with 2 condensed cycles specified in a group consisting of naphthalinyl, indenyl and dihydroindenyl, hexahydroindenyl, octahydroindenyl, wherein each can be substituted by a substitute specified in a group consisting of RE, RF and RJ, and RE means hydroxy, oxo; RF means C1-3alkyl substituted by C1-4alkylsulphonylamino, imino, wherein imino is substituted by a C1-4alkylsulphonylamino group; and RJ means an alkylsulphonylamino group; or L is specified in a group consisting of C(RA) = C(RB), wherein RA and RB mean a hydrogen atom, and R4 is specified in a group consisting of C6carbocyclyl specified in phenyl substituted by RJ having the above value.
EFFECT: higher efficacy of the compound.
16 cl, 2 tbl, 52 ex