MD4505C1 - Process for the synthesis of 3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one - Google Patents
Process for the synthesis of 3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one Download PDFInfo
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- MD4505C1 MD4505C1 MDA20160146A MD20160146A MD4505C1 MD 4505 C1 MD4505 C1 MD 4505C1 MD A20160146 A MDA20160146 A MD A20160146A MD 20160146 A MD20160146 A MD 20160146A MD 4505 C1 MD4505 C1 MD 4505C1
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- acetone
- dimethyl
- butan
- triazol
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- 238000000034 method Methods 0.000 title claims abstract description 17
- FMWWRALTYIWZEB-UHFFFAOYSA-N 3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound CC(C)(C)C(=O)CN1C=NC=N1 FMWWRALTYIWZEB-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 title abstract description 7
- 238000003786 synthesis reaction Methods 0.000 title abstract description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 38
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 14
- 238000009835 boiling Methods 0.000 claims abstract description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 7
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002244 precipitate Substances 0.000 claims abstract description 5
- 235000015320 potassium carbonate Nutrition 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 3
- 239000013049 sediment Substances 0.000 claims 1
- 230000002365 anti-tubercular Effects 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 230000000855 fungicidal effect Effects 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000011541 reaction mixture Substances 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- -1 Triazolyl ketone Chemical class 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000003852 triazoles Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical class BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000005283 haloketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 1
- 229960001225 rifampicin Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Invenţia se referă la chimia organică, şi anume la prepararea 3,3-dimetil-1-(1H-1,2,4-triazol-1-il)butan-onei 1, care poate fi aplicată ca un intermediar la sinteza unor compuşi cunoscuţi sau noi cu activitate fungicidă sau antituberculoasă. The invention relates to organic chemistry, namely to the preparation of 3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-one 1, which can be applied as an intermediate in the synthesis of some compounds known or new with fungicidal or antituberculosis activity.
C8H13N3O C8H13N3O
În literatura de specialitate sunt cunoscute substanţe cu activitate antituberculoasă şi fungicidă, care în molecula lor conţin inelul triazolic [1, 2]. Triazolilcetona 1 a fost utilizată ca precursor în sinteza unui şir de compuşi cu activitate fungicidă şi de reglare a creşterii plantelor [3]. După mai multe studii de cercetare efectuate de solicitant au fost descoperite proprietăţi noi, şi anume antituberculoase, la unii compuşi obţinuţi pornind de la triazolilcetona 1. Substances with antituberculosis and fungicidal activity are known in the specialized literature, which contain the triazole ring in their molecule [1, 2]. Triazolyl ketone 1 was used as a precursor in the synthesis of a series of compounds with fungicidal activity and plant growth regulation [3]. After several research studies carried out by the applicant, new properties, namely anti-tuberculosis, were discovered in some compounds obtained starting from triazolyl ketone 1.
Este cunoscut procedeul de obţinere a cetonei 1, care se foloseşte la producerea fungicidelor şi include alchilarea 1,2,4-triazolului cu bromură de pinacolină în mediu etanolic în prezenţa etoxidului de sodiu [4]. The procedure for obtaining ketone 1 is known, which is used in the production of fungicides and includes the alkylation of 1,2,4-triazole with pinacoline bromide in an ethanol medium in the presence of sodium ethoxide [4].
Alt procedeu de obţinere a triazolilcetonei 1 constă în alchilarea triazolului cu clorură de pinacolină şi necesită preventiv pregătirea soluţiei de metoxid de sodiu [5]. Another process for obtaining the triazolyl ketone 1 consists in the alkylation of the triazole with pinacoline chloride and requires the preventive preparation of the sodium methoxide solution [5].
Ambele procedee necesită preventiv pregătirea soluţiei de metoxid ori etoxid de sodiu, totodată în ambele procedee se foloseşte sodiu metalic. Reacţia decurge în mediu metanolic, care reprezintă un reagent foarte toxic. Both processes require the preventive preparation of sodium methoxide or ethoxide solution, at the same time in both processes metallic sodium is used. The reaction takes place in a methanol medium, which is a very toxic reagent.
Sunt cunoscute procedee de obţinere a triazolilcetonei 1, care constă în alchilarea 1,2,4-triazolului cu halogen-cetone la fierbere, într-un şir de diferiţi solvenţi, în prezenţa substanţelor neutralizatoare de acizi, inclusiv cu utilizarea sistemului acetonă/carbonat de potasiu [6,7]. Randamentul procedeelor descrise, de exemplu, pornind de la bromcetone nu este mai mare de 80…88%, iar reacţia de alchilare decurge 15 ore în sistemul acetonă/carbonat de potasiu. Totodată în aceste procedee pentru izolarea compusului 1 se foloseşte metoda de cromatografiere pe coloană sau cristalizarea, fapt ce contribuie la o complicare a procedeelor propuse şi la o reducere a randamentului final. There are known processes for obtaining triazolyl ketone 1, which consists in the alkylation of 1,2,4-triazole with halogen-ketones at boiling, in a series of different solvents, in the presence of acid neutralizing substances, including the use of the acetone/carbonate system potassium [6,7]. The yield of the processes described, for example, starting from bromoketones is not higher than 80...88%, and the alkylation reaction takes 15 hours in the acetone/potassium carbonate system. At the same time, in these procedures for the isolation of compound 1, the column chromatography or crystallization method is used, a fact that contributes to a complication of the proposed procedures and to a reduction of the final yield.
Problema pe care o rezolvă invenţia dată constă în elaborarea unui procedeu de sinteză a triazolilcetonei 1 prin alchilare în sistemul acetonă/carbonat de potasiu cu un randament mărit şi cu o durată mai mică de realizare a reacţiei. The problem that the given invention solves consists in the development of a process for the synthesis of triazolyl ketone 1 by alkylation in the acetone/potassium carbonate system with an increased yield and with a shorter duration of the reaction.
Esenţa invenţiei revendicate constă în elaborarea unui procedeu de sinteză a 3,3-dimetil-1-(1H-1,2,4-triazol-1-il)butan-2-onei din 1-clor-3,3-dimetil-2-butan, conform schemei: The essence of the claimed invention consists in the development of a process for the synthesis of 3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one from 1-chloro-3,3-dimethyl- 2-butane, according to the scheme:
Procedeul de obţinere a 3,3-dimetil-1-(1H-1,2,4-triazol-1-il)butan-2-onei include fierberea timp de 8…15 min a unei soluţii de 1H-1,2,4-triazol (1 parte) în acetonă, care conţine K2CO3 (1,09 părţi), după care se adaugă treptat o soluţie de 1-clor-3,3-dimetil-2-butan (1 parte) în acetonă, părţile fiind luate în raportul molar respectiv, amestecul reactant se fierbe timp de 5…7 ore, precipitatul rezidual se separă de soluţia acetonică a produsului final obţinut, acetona se distilează, produsul final se extrage cu hexan, din care la răcire se sedimentează produsul pur (1), cu un randament de 99%. The process for obtaining 3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one includes boiling for 8...15 min a solution of 1H-1,2, 4-triazole (1 part) in acetone, containing K2CO3 (1.09 parts), after which a solution of 1-chloro-3,3-dimethyl-2-butane (1 part) in acetone is gradually added, the parts being taken in the respective molar ratio, the reactant mixture is boiled for 5...7 hours, the residual precipitate is separated from the acetone solution of the final product obtained, the acetone is distilled, the final product is extracted with hexane, from which the pure product (1 ), with a yield of 99%.
Reacţia decurge într-o singură etapă cu un randament foarte bun (99%), aproape cantitativ. Triazolilcetona 1 este o substanţă care se dizolvă uşor în solvenţi organici şi în apă. S-a depistat că izolarea ei efectivă din amestecul reactant se poate face cu hexan la fierbere, acest factor a contribuit la obţinerea compusului 1 cu un randament foarte înalt şi cu o puritate suficientă. Ca rezultat compusul 1 nu necesită o purificare suplimentară. The reaction proceeds in a single step with a very good yield (99%), almost quantitative. Triazolylketone 1 is a substance that dissolves easily in organic solvents and water. It was found that its effective isolation from the reactant mixture can be done with boiling hexane, this factor contributed to obtaining compound 1 with a very high yield and sufficient purity. As a result compound 1 does not require further purification.
Utilizarea anume a clorpinacolinei în calitate de halogencetonă iniţială, efectuarea reacţiei de alchilare în sistemul acetonă/carbonat de potasiu şi utilizarea hexanului la izolarea produsului final sunt factori esenţiali pentru a atinge randamentul de 99%, totodată durata reacţiei fiind de două ori mai scurtă, comparativ cu procedeul din stadiul tehnicii. The particular use of chlorpinacoline as the starting haloketone, the performance of the alkylation reaction in the acetone/potassium carbonate system and the use of hexane to isolate the final product are essential factors to reach the 99% yield, while the reaction time is twice as short, compared with the procedure from the state of the art.
Exemplu de realizare a invenţiei Example of realization of the invention
La soluţia constituită din 6,9 g (0,1 mol) 1H-1,2,4-triazol şi 50 mL acetonă se adaugă 15,1 g (0,109 mol) K2CO3, amestecul se fierbe timp de 10 min, ulterior se adaugă cu picătura soluţia alcătuită din 13,4 g (0,1 mol) 1-clor-3,3-dimetil-2-butan în 20 mL acetonă. Amestecul reactant se fierbe timp de 5…7 ore (control CSS). Precipitatul format se filtrează, spălându-se minuţios, pe filtru, cu acetonă. Soluţia acetonică se distilează, reziduul obţinut se extrage cu hexan la fierbere, după răcirea hexanului se izolează un precipitat alb 16,5 g (99%) de 3,3-dimetil-1-(1H-1,2,4-triazol-1-il)butan-2-onă 1. To the solution consisting of 6.9 g (0.1 mol) 1H-1,2,4-triazole and 50 mL acetone, add 15.1 g (0.109 mol) K2CO3, boil the mixture for 10 min, then add dropwise the solution consisting of 13.4 g (0.1 mol) 1-chloro-3,3-dimethyl-2-butane in 20 mL acetone. The reaction mixture is boiled for 5...7 hours (CSS control). The formed precipitate is filtered, thoroughly washing the filter with acetone. The acetone solution is distilled, the residue obtained is extracted with boiling hexane, after cooling the hexane a white precipitate is isolated 16.5 g (99%) of 3,3-dimethyl-1-(1H-1,2,4-triazol- 1-yl)butan-2-one 1.
Randamentul reacţiei este de 99% (16,5 g), p.t.=65…67°C. The yield of the reaction is 99% (16.5 g), m.p.=65...67°C.
Structura compusului a fost confirmată pe baza analizei elementelor şi datelor spectrale: C8H13N3O, M=167,21. The structure of the compound was confirmed based on element analysis and spectral data: C8H13N3O, M=167.21.
Calculat,(%): C, 57,46; H, 7,84; N, 25,13. Calculated, (%): C, 57.46; H, 7.84; N, 25,13.
Găsit,(%): C, 57,49; H, 7,68; N, 24.99. IR (ν, cm-1): 680,3; 742,2; 883,4; 1020,3; 1034,7; 1135,9; 1210,2; 1275,3; 1363,8; 1470,7; 1508,4; 1595,2; 1719,9; 2948,7; 2977,5; 3114,9. Found, (%): C, 57.49; H, 7.68; N, 24.99. IR (ν, cm-1): 680.3; 742.2; 883.4; 1020.3; 1034.7; 1135.9; 1210.2; 1275.3; 1363.8; 1470.7; 1508.4; 1595.2; 1719.9; 2948.7; 2977.5; 3114.9.
Spectrul RMN 1H (400 MHz, CDCl3, δ, ppm, J/Hz ): 1,24 (s, 9H, Bu), 5,16 (s, 2H, N-CH2), 7,91 (s, 1H, triazol), 8,1(s, 1H, triazol). 1H NMR spectrum (400 MHz, CDCl3, δ, ppm, J/Hz ): 1.24 (s, 9H, Bu), 5.16 (s, 2H, N-CH2), 7.91 (s, 1H, triazole), 8.1(s, 1H, triazole).
Spectrul RMN 13C (100 MHz, CDCl3, δ, ppm): 206,25, 151,69, 144,74, 53,17, 43,49, 26,05. 13 C NMR spectrum (100 MHz, CDCl 3 , δ, ppm): 206.25, 151.69, 144.74, 53.17, 43.49, 26.05.
Exemplu de aplicare a compusului sintetizat Example of application of the synthesized compound
Cetona 1 - 3,3-dimetil-1-(1H-1,2,4-triazol-1-il)butan-2-onă poate fi aplicată în calitate de compus iniţial la obţinerea compuşilor cu activitate biologică antituberculoasă sau fungicidă. The 1-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one ketone can be applied as a starting compound to obtain compounds with antitubercular or fungicidal biological activity.
Drept exemplu serveşte procedeul de sinteză stereospecifică a (Z)-4,4-dimetil-1-(4-nitrofenil)-2-(1H-1,2,4-triazol-1-il)pent-1-en-3-onei - compus cu acţiune antituberculoasă. An example is the stereospecific synthesis process of (Z)-4,4-dimethyl-1-(4-nitrophenyl)-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3 -onei - compound with antituberculosis action.
La soluţia alcătuită din 1,67 g (0,01 mol) de triazolil-cetona - 3,3-dimetil-1-(1H-1,2,4-triazol-1-il)butan-2-onă (1) şi 1,66 g (0,011mol) para-nitro-benzaldehidă în 300 mL benzen se adaugă piperidină/acid acetic în cantităţi catalitice. Amestecul se fierbe timp de 5…7 ore (controlat periodic cu ajutorul CSS) cu distilarea azeotropă a apei formate, folosind aparatul Dean-Stark, apoi soluţia de benzen se răceşte până la temperatura camerei, rămăşiţele de catalizator se extrag cu apă, apoi soluţia benzenică a produsului final se usucă cu Na2SO4. Solventul se distilează, iar reziduul se recristalizează din etanol. To the solution consisting of 1.67 g (0.01 mol) of triazolyl ketone - 3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one (1) and 1.66 g (0.011 mol) of para-nitro-benzaldehyde in 300 mL of benzene is added catalytic amounts of piperidine/acetic acid. The mixture is boiled for 5...7 hours (controlled periodically with CSS) with the azeotropic distillation of the formed water, using the Dean-Stark apparatus, then the benzene solution is cooled to room temperature, the catalyst remains are extracted with water, then the solution benzene of the final product is dried with Na2SO4. The solvent is distilled off and the residue is recrystallized from ethanol.
Randamentul reacţiei este de 70% (2,1 g), p.t.= 114…116°С. The yield of the reaction is 70% (2.1 g), m.t.= 114...116°С.
Structura compusului este confirmată pe baza analizei elementelor şi datelor spectrale : C15H16N4O3, M=300,31. The structure of the compound is confirmed based on elemental analysis and spectral data: C15H16N4O3, M=300.31.
Compusul posedă activitate antituberculoasă la nivelul remediului cunoscut Rifampicina. The compound possesses antituberculosis activity at the level of the well-known remedy Rifampicin.
1. Rangappa S. Keri, Siddappa A. Patil, Srinivasa, Budagumpi, Bhari Mallanna Nagaraja. Triazole: A Promising Antitubercular Agent. Chem Biol Drug Des 2015, 86, 410-423 1. Rangappa S. Keri, Siddappa A. Patil, Srinivasa, Budagumpi, Bhari Mallanna Nagaraja. Triazoles: A Promising Antitubercular Agent. Chem Biol Drug Des 2015, 86, 410-423
2. Pawan Kumar Mishra, Jaya Dwivedi, Rajani Chauhan. Triazoles as potential antitubercular agent: a review. Journal of Advanced Scientific Research, 2016, 7(1), 9-13. 2. Pawan Kumar Mishra, Jaya Dwivedi, Rajani Chauhan. Triazoles as potential antitubercular agents: a review. Journal of Advanced Scientific Research, 2016, 7(1), 9-13.
3. Funaki Y. et al. Structure-activity relationships of vinyl triazole fungicides. J. Pesticide Sci., 1984, 9, 229-236 3. Funaki Y. et al. Structure-activity relationships of vinyl triazole fungicides. J. Pesticide Sci., 1984, 9, 229-236
4. US 4243405 A 1981.01.06 4. US 4243405 A 1981.01.06
Description: column 6 Description: column 6
5. CN 102351803 A 2012.02.15 (SUZHOU CHENGHE PHARMACEUTICAL & CHEMICAL CO LTD) 5. CN 102351803 A 2012.02.15 (SUZHOU CHENGHE PHARMACEUTICAL & CHEMICAL CO LTD)
Description (Espacenet translation in english) Description (Espacenet translation in English)
6. CA 1168248 A1984-05-29 (Bayer AG) 6. CA 1168248 A1984-05-29 (Bayer AG)
Description: pag. 14-15; pag. 30 lines 14-22; pag. 33 lines 23-26; pag. 34 lines 1-7; pag. 36 lines 1-10; Description: pages 14-15; page 30 lines 14-22; page 33 lines 23-26; page 34 lines 1-7; page 36 lines 1-10;
7. GB 1464224 A 1977-02-09 (BAYER AG) 7. GB 1464224 A 1977-02-09 (BAYER AG)
Description: pag. 2, lines 18-26; pag. 4, lines 60-65 and pag. 5, lines 1-15; pag. 13, example 2; pag. 16, Example No.19; Claims 6 Description: page 2, lines 18-26; page 4, lines 60-65 and page 5, lines 1-15; page 13, example 2; page 16, Example No. 19; Claims 6
Claims (1)
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| MDA20160146A MD4505C1 (en) | 2016-12-21 | 2016-12-21 | Process for the synthesis of 3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20160146A MD4505C1 (en) | 2016-12-21 | 2016-12-21 | Process for the synthesis of 3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one |
Publications (2)
| Publication Number | Publication Date |
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| MD4505B1 MD4505B1 (en) | 2017-08-31 |
| MD4505C1 true MD4505C1 (en) | 2018-03-31 |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1464224A (en) * | 1974-06-29 | 1977-02-09 | Bayer Ag | Triazolyl-alkanones and triazolylalkanols processes for their preparation and their use as fungicides |
| US4079143A (en) * | 1975-08-26 | 1978-03-14 | Imperial Chemical Industries Limited | Fungicidal 1H-1,2,4-triazoles |
| US4243405A (en) * | 1976-08-19 | 1981-01-06 | Imperial Chemical Industries Limited | Fungicidal compounds |
| CA1168248A (en) * | 1980-07-25 | 1984-05-29 | Erik Regel | Triazolylpropenol derivatives, a process for their preparation and their use as plant growth regulators and fungicides |
| CA1179352A (en) * | 1980-07-25 | 1984-12-11 | Erik Regel | Triazolylpropenone derivatives, a process for their preparation and their use as intermediates |
| US4554007A (en) * | 1979-03-20 | 1985-11-19 | Sumitomo Chemical Company, Limited | Geometrical isomer of 1-substituted-1-triazolylstyrenes, and their production and use as fungicide, herbicide and/or plant growth regulant |
| CN102351803A (en) * | 2011-11-18 | 2012-02-15 | 苏州诚和医药化学有限公司 | Method for synthesizing 3,3-dimethyl-1-(1H-1,2,4-triazole-1-yl)-2-butanone |
-
2016
- 2016-12-21 MD MDA20160146A patent/MD4505C1/en not_active IP Right Cessation
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1464224A (en) * | 1974-06-29 | 1977-02-09 | Bayer Ag | Triazolyl-alkanones and triazolylalkanols processes for their preparation and their use as fungicides |
| US4079143A (en) * | 1975-08-26 | 1978-03-14 | Imperial Chemical Industries Limited | Fungicidal 1H-1,2,4-triazoles |
| US4243405A (en) * | 1976-08-19 | 1981-01-06 | Imperial Chemical Industries Limited | Fungicidal compounds |
| US4554007A (en) * | 1979-03-20 | 1985-11-19 | Sumitomo Chemical Company, Limited | Geometrical isomer of 1-substituted-1-triazolylstyrenes, and their production and use as fungicide, herbicide and/or plant growth regulant |
| US4749716A (en) * | 1979-03-20 | 1988-06-07 | Sumitomo Chemical Company, Limited | Geometrical isomer of 1-substituted-1-triazolystyrenes |
| CA1168248A (en) * | 1980-07-25 | 1984-05-29 | Erik Regel | Triazolylpropenol derivatives, a process for their preparation and their use as plant growth regulators and fungicides |
| CA1179352A (en) * | 1980-07-25 | 1984-12-11 | Erik Regel | Triazolylpropenone derivatives, a process for their preparation and their use as intermediates |
| CN102351803A (en) * | 2011-11-18 | 2012-02-15 | 苏州诚和医药化学有限公司 | Method for synthesizing 3,3-dimethyl-1-(1H-1,2,4-triazole-1-yl)-2-butanone |
Non-Patent Citations (3)
| Title |
|---|
| Funaki Y. et al. Structure-activity relationships of vinyl triazole fungicides. J. Pesticide Sci., 1984, 9, 229-236 * |
| Pawan Kumar Mishra, Jaya Dwivedi, Rajani Chauhan. Triazoles as potential antitubercular agent: a review. Journal of Advanced Scientific Research, 2016, 7(1), 9-13. * |
| Rangappa S. Keri, Siddappa A. Patil, Srinivasa, Budagumpi, Bhari Mallanna Nagaraja. Triazole: A Promising Antitubercular Agent. Chem Biol Drug Des 2015, 86, 410-423 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4505B1 (en) | 2017-08-31 |
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| MM4A | Patent for invention definitely lapsed due to non-payment of fees |