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Microwave synthesis of sulfanilic acid

Havlíček J., Myška K., Tejchman W., Karásková N., Doležal R., Maltsevskaya N. V., Kolář K.

Chemistry-Didactics-Ecology-Metrology

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2017

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R. 22, NR 1-2

93--98

EN

Sulfanilic acid represents an important substance, which is frequently utilized in the industry of azo dyes as well as in drug development of antimicrobials (e.g. of sulfonamides). Students can also meet with such type of compounds in chemistry labs, for example, when they estimate pH by methyl orange indicator or prepare Orange II for textile colouring. Both of these dyes are products of azo coupling of sulfanilic acid as diazonium salt with N,N-dimethylaniline or 2-naphthol, respectively. In the article, we focus on the synthesis of sulfanilic acid as a well-known experiment in the organic chemistry education. The synthesis was modified as the solvent free and microwave assisted experiment under semimicroscale conditions. That experiment is very convenient for the organic chemistry courses in the university or the high school teaching.

PL

Kwas sulfanilowy stanowi ważną substancję, często stosowaną w przemyśle barwników azowych, jak również w produkcji leków przeciwdrobnoustrojowych (np. sulfonamidów). Studenci mogą również spotykać się z takimi związkami w laboratoriach chemicznych, na przykład przy oznaczaniu pH z wykorzystaniem oranżu metylowego lub przy przygotowywaniu Oranżu II dla przemysłu tekstylnego. Oba te barwniki są produktami sprzężenia soli diazoniowych kwasu sulfanilowego odpowiednio z N,N-dimetyloaniliną lub 2-naftolem. W artykule przedstawiono syntezę kwasu sulfanilowego jako przykład dobrze znanego eksperymentu w edukacji chemii organicznej. Syntezę zmodyfikowano jako reakcję bez rozpuszczalników i wspomagano mikrofalowo w warunkach półmikropreparacji. Eksperyment ten powinien być przedstawiany podczas kursów chemii organicznej na uniwersytecie lub w szkole średniej.

2

Nowa bezrozpuszczalnikowa metoda syntezy olanzapiny i jej pochodnych

Jaśkowska J., Kułaga D., Majka Z.

Przemysł Chemiczny

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2016

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T. 95, nr 10

1918--1920

PL

Opracowano nową bezrozpuszczalnikową metodę syntezy olanzapiny w reakcji jodku metylu i N-demetyloolanzapiny (2-metylo-4-(piperazyn-1-ylo)-10H-tieno[2,3-b][1,5]benzodiazepiny) w warunkach promieniowania mikrofalowego. Reakcję prowadzono w obecności węglanu potasu, bromku tertbutyloamoniowego oraz niewielkich ilości dimetyloform- amidu. Uniwersalność i skuteczność nowej metody potwierdzono w syntezie wybranych pochodnych olanzapiny.

EN

2-Methyl-4-(1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine (N-demethylolanzapine) was alkylated witch MeI in presence of K₂CO₃, Bu4NBr and DMF at room temp. in microvawe field to olanzapine and its derivatives. The addn. of DMF resulted in increasing the product yield. The maximum product yield 64% and purity (after 15 s) were reached at equi-mol. N-demetylolanzapine/Mel ratio.

3

Solvent-free synthesis and assessment of substituent effects from IR & NMR spectra of some substituted benzylidene-5-ethyl-1,3,4-thiadiazole-2-amines

Thirunarayanan G.

International Letters of Chemistry, Physics and Astronomy

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2014

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Vol. 5

89--98

EN

A series containing ten titled compounds were synthesized by SiO2:H3PO4 catalyzed solvent-free condensation of substituted benzaldehydes and 2-amino-5-ethyl-1,3,4-thiadiazole under microwave irradiation. The yields of prepared amines are more than 90 %. The synthesized amines were characterized by their physical constants and spectroscopic data reported in literature earlier for known compounds. The assigned spectral group frequencies such as infrared νC=N, C-S-C, N-N (cm-1) and NMR chemical shifts (δ, ppm) of CH, C=N have been correlated with Hammett substituent constants, F and R parameters using single and multi-linear regression analysis. From the results of statistical analyses, the effects of substituent on the above spectral data have been discussed.

4

Synthesis, spectral correlations and antimicrobial activities of some 2-hydroxyphenyl-styrylketone

Sathiyamoorthi K., Mala V., Suresh R., Sakthinathan S.P., Kamalakkannan D., Ranganathan K., Arulkumaran R., Sundararajan R., Vijayakumar S., Vanangamudi G., Thirunarayanan G.

International Letters of Chemistry, Physics and Astronomy

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2013

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Vol. 7, iss. 2

102--119

EN

Some 2’-hydroxyphenylchalcones have been synthesized under microwave irradiation by Claisen-Schmidt condensation between substituted 2-hydroxyacetophenone and substituted benzaldehydes using catalytic amount of SiO2-H3PO4. These chalcones were established by their physical constants and spectroscopic data published earlier. The UV, IR, 1H NMR and 13C NMR spectral data of these chalcone have correlated with Hammett substituent constants, F and R parameters. All the compounds have been subjected to screened for antimicrobial activity.

5

Preheated fly-ash catalyzed cyclization ofchalcones: Synthesis of some substituted pyrazole-1-carbothioamides and spectral correlations in 3-(3,4-dichlorophenyl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazole-1 carbothioamides

Thirunarayanan G., Sekar K. G.

International Letters of Chemistry, Physics and Astronomy

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2013

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Vol. 10, iss. 1

18-34

EN

Some substituted 1-thiocarbomyl pyrazolines including 3-(3,4-dichlorophenyl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamides using solvent-free preheated fly-ash catalyzed cyclization between chalcones and thiosemicarbazide microwave irradiation. The yields of these thiocarbomyl pyrazolines are more than 80 %. The purities of these synthesised pyrazoline derivatives are checked by their physical constants and spectral data earlier reported in the literature The spectral data of these 3-(3,4-dichlorophenyl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamides had been correlated, using single and multi-linear regression analysis.