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4 protocols using phosphoryl chloride

1

Synthesis of Organic Compounds

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Meta-aminophenol, para-aminophenol, 4-hydroxycoumarin, acetic acid, methanol, ethanol, toluene, acetone, dimethyl sulfoxide, potassium-tetrachloridopalladate(II), and phosphoryl chloride were obtained from Sigma-Aldrich, Germany.
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2

Chiral Amines and Silica Nanoparticle Synthesis

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Phosphoryl chloride (POCl3, 99%), (R)-(+)-α-methylbenzylamine (RMBA, 98%), (S)-(−)-α-methylbenzylamine (SMBA, 98%) and (±)-α-methylbenzylamine (MBA, 98%) were bought from Sigma-Aldrich. Methanol, ethanol, tetrahydrofuran (THF), sodium chloride (NaCl), ferric chloride hexahydrate (FeCl3·6H2O), ferrous chloride tetrahydrate (FeCl2·4H2O), ammonium hydroxide (25% (w/w)), glycerol, tetraethyl orthosilicate (TEOS), 3-aminopropyltrimethoxysilane (APTMS), dl-tartaric acid (99%), dl-phenylalanine (99%), dl-valine (99%) and triethylamine (TEA, 99%) were purchased from Merck.
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3

Synthesis of Heterocyclic Compounds

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All experiments were carried out in an atmosphere of dry argon, and flasks were flame dried. Solvents were dried by usual methods (diphenyl ether, diethyl ether, and THF over benzophenone ketyl, CHCl3, and CH2Cl2 over P4O10, hexane over sodium-potassium alloy) and distilled. Chromatographic purification was carried out on silica gel 60 (0.15–0.3 mm, Macherey-Nagel GmbH & Co. KG, Düren, Germany). Sodium hydride (dry, 95%), potassium tert-butoxide, trimethyl orthoformate, 2-iso-propylaniline, 2-(tert-butyl)aniline, 2-nitroaniline, phosphoryl chloride, 9H-carbazole, Meldrum’s acid, acrolein, and crotonaldehyde were purchased from Sigma-Aldrich (Poznań, Poland), and were used without further purification.
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4

Reagent Preparation and Purification for Organic Synthesis

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All experiments were carried out in an atmosphere of dry argon, and flasks were flame dried. Solvents were dried by usual methods (diphenyl ether, diethyl ether, and THF over benzophenoneketyl, CHCl3, and CH2Cl2 over P4O10, hexane, and pyridine over sodium-potassium alloy) and distilled. Chromatographic purification was carried out on silica gel 60 (0.15–0.3 mm, Macherey-Nagel GmbH & Co. KG, Dueren, Germany). Crotonaldehyde, 4a,12a-dihydro-12H-benzo[5,6][1,4]thiazino[2,3-b]quinoxaline, N1,N1-dimethylbenzene-1,4-diamine, 2,2-dimethylpropane-1,3-diol, 10H-phenothiazine, phosphoryl chloride, 2-isopropylaniline, isoquinolin-5-amine, quinolin-5-amine, sodium hydride (dry, 95%), stannous chloride, silver carbonate on Celite and o-toluidine were purchased from Sigma–Aldrich (Poznań, Poland), and were used without further purification.
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