N-(-alkoxyalkyl)caprolactam with insectrepellent activity
(57) Abstract:Usage: biologically active substances, derivatives of E-caprolactam with insectrepellent activity. The inventive product - N - a - alkoxyalkyl/caprolactam General formula , where R=C3H7when R1= C2H5C3H7C4H9. Reagent 1: - caprolactam, reagent 2: oil aldehyde reagent 3: ethanol, propanol or butanol. Reaction conditions: mixing of reagents in the environment of benzene with sulfuric acid as catalyst at room temperature, exposure of the reaction mass 33 h and neutralized with soda. Distillation in vacuum. N/ a-ethoxymethyl/caprolactam, BF C12H23O2the yield is 50%, so Kip. 106 - 108°C SMM. 3 table. The invention relates to new biologically active compounds, namely N-( -alkoxyalkyl)caprolactam General formula
N - H - OR1where R=C3H7when R1=C2H5-C4H9with insectrepellent activity.The closest structural analogues of the claimed compounds are N-( -alkoxyalkyl)caprolactam (1,2), which are used as intermediates to obtain tert-N-vinyl is), showing insectrepellent action.The goal is to find new substances exhibiting insectrepellent activity of long duration.N-( -Alkoxyalkyl)caprolactam produced by interaction of caprolactam with oily aldehyde and the corresponding alcohols in the presence of conc. H2SO4at room temperature.P R I m e R 1. Obtaining N-( - ethoxymethyl)caprolactam.To a solution of 25 g (0,22 mol) of caprolactam, of 23.8 g (of 0.33 mole) of butyric aldehyde and 15.2 g (of 0.33 mole) of ethanol and 125 ml of benzene at room temperature and stirring, slowly add 1 ml conc. H2S4. A mixture of 33 h at the same temperature. Then the reaction mass is washed with a solution of potash, water. After removal of the solvent the residue is distilled in vacuum. Get to 23.4 g (50%) substances with so Kip. 106-108aboutC/3 mm; n2D51.4630; d2400.9782 .Found, %: N 6,28.C12H23NO2.Calculated, %: N 6,57.In the IR spectrum of compound has absorption bands: C=Oat 1650 cm-1andC-O-Cwhen 1100-1105 cm-1.Similarly receive the remaining connections (see tab. 1)drugs on cotton diagonal in the amount of 40 g of active substance per 1 m2. As biotests used mosquito edes aegyti and fleas nsilla cheois field - mosquito natural populations of A. mmunis dominant in Moscow and Tyumen regions. Reference taken is known repellent DEATH metal. The effectiveness of the compounds expressed by the factor deterring actions (CODE) by the formula 100 (A-B)/A, where a is the number of mosquito landings for 5 min to test the control (untreated) fabric B on the test fabric treated with the drug. In the case of fleas: a - the number of fleas remaining specific exposure on a clean (control) sample, B is the same on impregnowana sample. The CODE is determined after 1 day after treatment of the fabric and then every 1-2 weeks to achieve CODE up to 70%.Acute toxicity to warm-blooded animals was determined by means of a single injection of the drug in the form of oil solution in the stomach to white rats. Statistical data processing was carried out according to the method of Cerberus.The results of the tests of repellent activity are presented in table. 2 and 3.Results of the tests show that the claimed compounds have a strong repellent effect. The increase in the length of the OTP is selskohozyaistvennyh animals from blood-sucking insects.The claimed compounds are promising for practical use due to the fact that the retrieval method is simple and clean. All raw materials refers to large-scale products of the chemical industry. N-( -Alkoxyalkyl)caprolactam General formula
N - H - OR1< / BR>where R is C3H7when R1- C2H5-C4H9,
with insectrepellent activity.
FIELD: chemistry of lactams' derivatives.
SUBSTANCE: the present innovation deals with obtaining N-(2-chloroalkyl)- and N-alkyl-aromatic derivatives of lactams of the following general formula: , where R=H, Cl, R'=(CH2)3, (CH2)5 which could be modifiers of unsaturated carbon-chain caoutchoucs and rubber mixtures based upon them. The suggested method for obtaining the mentioned N-substituted lactams deals with combining N-chlorolactams and allyl benzene, moreover, as N-lactams one should apply either N-chlorobutyrolactam or N-chlorocaprolactam. The process should be carried out at molar ratio of N-chlorolactam to allyl benzene being equal to 1-1.15:1, at availability of a catalyzer as mono-tertiary-butylperoxy-α-methylmethoxyethoxyethyl ether of ethylene glycol taken at the quantity of 0.4-4.0% weight, in the medium of inert solvent, for example, chlorobenzene at 100-125° C for about 15-20 min. The innovation enables to shorten terms of reaction by 20-30 times, simplify the way for obtaining target products and widen the assortment of the obtained compounds, as well.
EFFECT: higher efficiency.
FIELD: organic chemistry, chemical technology.
SUBSTANCE: invention relates to technology for preparing caprolactam by the cyclization reaction of derivatives of aminocaproic acid. Method is carried out by cyclizing hydrolysis of compound chosen from the group comprising aminocaproic acid esters or amides, or their mixtures. The process is carried out in the presence of water, in vapor phase at temperature 200-450°C in the presence of a solid catalyst comprising of aluminum oxide that comprises at least one macroporosity with pores volume corresponding to pores with diameter above 500 Å taken in the concentration 5 ml/100 g of above. Preferably, the specific square of catalyst particles is above 10 m2/g and the total volume of pores is 10 ml/100 g or above wherein pores volume corresponds to pores with diameter above 500 Å is 10 ml/100 g or above. Invention provides improving the process indices due to the improved properties of the solid catalyst.
EFFECT: improved preparing method.
5 cl, 2 ex
FIELD: organic chemistry, medicine, biochemistry, pharmacy.
SUBSTANCE: invention relates to novel azaheterocycles of the general formula (I): possessing inhibitory effect on activity of tyrosine kinase and can be used in treatment of different diseases mediated by these receptors. In compound of the general formula (1) W represents azaheterocycle comprising 6-13 atoms that can be optionally annelated with at least one (C5-C7)-carbocycle and/or possibly annelated with heterocycle comprising 4-10 atoms in ring and comprising at least one heteroatom chosen from oxygen (O), sulfur (S) or nitrogen (N) atom; Ra 1 represents a substitute of amino group but not hydrogen atom, such as substituted (C1-C6)-alkyl, possibly substituted aryl and possibly substituted 5-10-membered heterocyclyl comprising at least one heteroatom chosen from O, S or N; Rb represents carbamoyl group -C(O)NHRa wherein Ra represents a substitute of amino group but not hydrogen atom, such as possibly substituted alkyl, possibly substituted aryl, possibly substituted 5-10-membered heterocyclyc comprising at least one heteroatom chosen from O, S or N; Rc represents a substitute of cyclic system, such as possibly substituted (C1-C6)-alkyl, possibly substituted aryl and possibly substituted 5-6-membered heterocyclyl comprising at least one heteroatom chosen from O, S or N; or Rb and Rc form in common aminocyanomethylene group [(=C(NH2)CN], or their pharmaceutically acceptable salts. Also, invention relates to methods for synthesis of these compounds (variants), a pharmaceutical composition, combinatory and focused libraries.
EFFECT: valuable medicinal properties of compounds and pharmaceutical composition, improved methods for synthesis and preparing.
35 cl, 16 sch, 13 tbl, 43 ex
SUBSTANCE: invention refers to bengamide derivatives produced by fermented microorganism Myxococcus virescens ST200611 (DSM 15898), to application in cancer therapy and/or prevention, to medical products containing bengamide derivatives, making process of bengamide of formula . In addition, the invention refers to compound of formula .
EFFECT: new bengamide derivatives are characterised with useful biological properties.
15 cl, 7 tbl, 18 ex
SUBSTANCE: invention relates to derivatives of 3-aminocaprolactam of formula (I): , where X represents -CO-R1 or -SO2-R2, R1 represents alkyl (with the exception of 5-methylheptanyl and 6-methylheptanyl, where radical R1 is bonded to carbonyl in position 1), halogenalkyl, alkoxy (with the exception of tret-butyloxy), alkenyl, alkinyl or alkylamino radical from 4-20 carbon atoms (for example, from 5-20 carbon atoms, 8-20 carbon atoms, 9-20 carbon atoms, 10-18 carbon atoms, 12-18 carbon atoms, 13-18 carbon atoms, 14-18 carbon atoms, 13-17 carbon atoms) and R2 is alkyl radical from 4-20 carbon atoms (for example, from 5-20 carbon atoms, 8-20 carbon atoms, 9-20 carbon atoms, 10-18 carbon atoms, 12-18 carbon atoms, 13-18 carbon atoms, 14-18 carbon atoms, 13-17 carbon atoms); or to its pharmacologically acceptable salt. Invention also relates to application and pharmacological composition, which has anti-inflammatory activity, based on said compounds.
EFFECT: obtaining new compounds and based on them pharmacological composition, which can be applied for obtaining medications for treatment, relief or prevention of inflammatory disease symptoms.
57 cl, 62 ex
SUBSTANCE: present invention relates to a method for synthesis of caprolactam from alkylcyanovalerate which involves bringing alkylcyanovalerate into contact with hydrogen in gaseous state in the presence of a hydrogenation catalyst and a ring formation catalyst, and treatment after condensation of a gaseous stream containing the formed lactam in order to separate ammonium which may be present, the formed alcohol and/or the caprolactam solvent and extraction of caprolactam, where the hydrogenation catalyst includes a metal element or a mixture of metal elements selected from a group containing an active metal element in form of iron, ruthenium, rhodium, iridium, palladium, cobalt, nickel, chromium, osmium and platinum or several metals from this list, and the ring formation catalyst is porous aluminium oxide.
EFFECT: obtaining caprolactam without intermediate separation of alkylaminocaproate.
10 cl, 5 ex, 1 tbl
FIELD: medicine, pharmaceutics.
SUBSTANCE: invention refers to compounds of general formula
where there are R3/R3', R4/R4' and R5/R5' where at least one of either R4/R4' or R5/R5' always represents a fluorine atom, and the other radical values are disclosed in the description.
EFFECT: making the compounds which are γ-secretase inhibitors, and can be effective in treating Alzheimer's disease or advanced cancers, including but not limited to carcinoma of uterine cervix and breast carcinoma and malignant tumours of hematopoietic system.
15 cl, 3 tbl, 18 ex
SUBSTANCE: invention relates to an improved method of purifying crude ε-caprolactam obtained from cyclohexanone oxime via gas phase Beckmann rearrangement, comprising a step for crystallisation of ε-caprolactam from the solution of crude ε-caprolactam in ether or halogenated hydrocarbon, a step for washing the crystalline ε-caprolactam obtained from the crystallisation step with a solvent and a step for hydrogenation of the crystalline ε-caprolactam through contact with hydrogen in the presence of a hydrogenation catalyst.
EFFECT: high purity of the product, high absorption of potassium permanganate and extraction coefficient at wavelength 290 nm equal to or less than 0,05, which meets all requirements for commercial products.
19 cl, 12 ex
SUBSTANCE: invention relates to methods of producing a prepolymer with functional groups via chemical modification of oligodiene diols, which are used in chemical industry as the basis for making tyres, industrial rubber articles and paint materials. Described is a method of producing a prepolymer with terminal amino groups, involving treating oligodiene diol with a modifier, followed by separation of the reaction product, via an oligomerisation reaction of ε-caprolactam with oligodiene diol in the presence of catalytic amounts of benzoic acid with reagents in molar ratio 4:1:0.005, respectively, in a vacuum-sealed ampoule at 170°C and reaction time of 180 minutes.
EFFECT: shorter reaction time and lower temperature and, as a result, fewer thermal-oxidative and destructive processes, possibility of using industrially available starting reagents.
SUBSTANCE: invention relates to a redox ammoximation method, wherein a ketone or aldehyde reacts with ammonia and oxygen in the presence of a catalyst, where the catalyst is a redox catalyst based on aluminophosphate, having a qualitative general formula M1M2AlPO-5 (I), where M1 denotes at least one transition metal selected from Co(III), Mn(III), Fe(III), Cr(VI), Cu(III), V(V) and Ru(III); M2 denotes a metal selected from Ge(IV), Sn(IV), Re(IV), V(IV) and mixtures thereof; M1 and M2 are different from each other; and a certain portion of phosphorus atoms in the structure of the type M1M2AlPO-5 is substituted with atoms of M2. Also disclosed is a redox ammoximation catalyst.
EFFECT: providing a selective ammoximation method.
11 cl, 5 tbl, 6 dwg, 16 ex