Tri-ethylamine

The submitters report that both l,4-diazabicyclo[2.2.2]octane and triethylamine have been used to catalyze this decomposition. Tri-ethylamine was less satisfactory as a catalyst because of its relatively rapid reaction with the solvent, carbon tetrachloride, to form triethylamine hydrochloride and because of difficulty encountered in separating triethylamine from the dicarbonate pi oduct. The 1,4-diazabicyclo-[2.2.2]octane was efficiently separated from the dicarbonate product by the procedure described in which the crude product was washed with very dilute aqueous acid. 

Note The pre- and post-treatment of the chromatograms with the basic tri-ethylamine solution, which can be replaced by an alcoholic solution of sodium hydroxide [1,4] or a phosphate buffer solution pH = 8.0 (c = 0.2 mol/1) [5], serves to stabilize the fluorescence of the amino derivatives [2]. A final spraying with methanolic hydrochloric acid (chci = 5 mol/1) or 70% perchloric acid renders the detection reaction highly specific for histamine [4] and for catecholamines and indolamines [5]. 

Treatment of a 3-aminotriazolopyridine with acid gave the imidazopyridine 242 (81T1787), also obtained from the 3-nitro derivative by catalytic reduction (83AHC79). Quaternary salts derived from compound 2, when treated with tri-ethylamine and subsequently heated give 2-pyridylcyanamides 243 or 2-(oxazol-l-yl)pyridines 244 depending on the alkyl group (86H(24)2563) the ylides are presumably intermediates (see also Section IV.I). 

When diazomethane is slowly added to excess lactam, the anions formed can interact with unreacted lactam by means of hydrogen bonds to form ion pairs similar to those formed by acetic acid-tri-ethylamine mixtures in nonpolar solvents. The methyldiazonium ion is then involved in an ion association wdth the mono-anion of a dimeric lactam which is naturally less reactive than a free lactam anion. The velocity of the Sn2 reaction, Eq. (7), is thus decreased. However, the decomposition velocity of the methyldiazonium ion, Eq. (6a), is constant and, hence, the S l character of the reaction is increased which favors 0-methylation. It is possible that this effect is also involved in kinetic dependence investigations have shown that with higher saccharin concentrations more 0-methylsaccharin is formed. 

A 0.60 g portion of N-carbobenzoxy-D-phenylglycine is dissolved in 10 ml of dry tetra-hydrofuran. The solution is cooled in an ice-salt bath, and to it is added 0.29 ml of tri-ethylamine with stirring over a period of 10 minutes, followed by 0.29 ml of isobutyl chloroformate, after which stirring is continued for 10 minutes at -5°C. During this time,... 

A mixture of 142.5 g of "Rosin Amine D" containing about 70% dehydroabietylamine and 30% dihydro and tetrahydroabietylamine, 47.0 g of ethylene dibromide, and 60.6 g of tri-ethylamine is dissolved in 350 cc of anhydrous xylene and refluxed for about 16 hours. Thereafter the triethylamine dibromide salt formed Is separated from the solution by filtering the cool reaction mixture and washing with ether. The solution is then concentrated under reduced pressure to dryness to remove the ether, xylene and excess triethylamines present. 

A solution of 3.55 parts of L-trypTtophanyl-L-methionyl-L-aspartyl-L-phenylalanine amide trifluoroacetate in 30 parts of dimethylformamide is cooled to 0 C, and 1.01 parts of tri-ethylamine are added. The mixture is stirred while 1.84 parts of N-tert-butyloxycarbonyl-(3-alanine 2,4,5-trichlorophenyl ester are added at 0 C. The reaction mixture is kept at 0°C for 48 hours and then at 20°-23°C for 24 hours. The mixture is added to a mixture of 100 parts of ice-water, 0.37 part of concentrated hydrochloric acid (SG 1.18), 1.2 parts of acetic acid and 20 parts of ethyl acetate. The mixture is stirred for 15 minutes at 0°-10°C and is then filtered. The solid residue is washed with water and then with ethyl acetate, and is dried at 40°-50°C under reduced pressure. There is thus obtained N-tert-butyloxycarbonyl-)3-alanyl-L-tryptophanyl-L-methionyl-L-aspartyl-L-phenylalanine amide, MP 213°C with decomposition. 

B. Diphenylcyclopropenone. A solution of 100 ml. of tri-ethylamine (Note 2) in 250 ml. of methylene chloride is magnetically stirred in a 2-1. one-necked flask while 108 g. (0.29 mole) of the above dibromoketone in 500 ml. of methylene chloride is added dropwise over 1 hour. The mixture is stirred for an additional 30 minutes and then extracted with two 150-ml. portions of 3N hydrochloric acid the aqueous extracts are discarded. The red organic solution is transferred to a 2-1. Erlen-... 

In-situ activation of carboxylic acids can be also carried out by Tos - Cl/tri-ethylamine, according to Fig. 7 ... 

Phenyl N-acetylcarbazate 1529 cyclizes on boiling with excess TCS 14/tri-ethylamine in toluene to give 5-methyl-l,3,4-oxadiazohne-2-one 1530 in 65-70% yield [41, 59, 60]. The same type of cyclization was subsequently described for re-... 

The use of the triphenylphosphine-carbon tetrachloride adduct for dehydration reactions appears to be a very simple way of synthesizing nitriles from amides, carbodi-imides from ureas, and isocyanides from monosubstituted formamides. All of these reactions involve the simultaneous addition of triphenylphosphine, carbon tetrachloride, and tri-ethylamine to the compound to be dehydrated. The elimination of the elements of water is stepwise. An adduct, e.g. (46), is first formed, chloroform being eliminated, which decomposes to produce hydrogen chloride and the dehydrated product. 

Figure 2, GC-TEA (N mode) chromatogram of a tire factory air sample. The column was a 5,5 m glass tube, 2mm, i,d, packed with Carbopak B(4% Carbowax 20 M, with 0,8% KOH on charcoal). Carrier gas flow rate was 15 mL/min, Column temperature was held at 40°C for 2 min, and then increased by 8°/min to 180°C, Peak identity 1-dimethylamine, 2-trimethylamine, 3-diethylamine, 4-tri-ethylamine, and 5-morpholine,...

It was only around 1850 that the first amines were discovered by Wurtz [2], who considered them as alkylated (or arylated) derivatives of NH3. Nowadays, it is well known that the amine function is widespread among biologically important compounds, but mostly it is present in polyfunctional molecules such as amino acids, alkaloids, etc. Simple amines are very rare in nature, with the exception of tri-ethylamine and the trimethylammonium ion which come from the putrefaction of proteins. 

Experimental Preparation of Spironaphthooxazine 33 (N-Bu). Tri-ethylamine (3.54 g, 35 mmol) was added to a suspension of 2,3,3-trimethyl-iV-butylindolinium iodide (12.0 g, 35 mmol) and o-nitrosonaphthol (6.1 g, 35 mmol) in EtOH (100 ml) under stirring. The mixture was refluxed for 2 h, cooled, and evaporated under reduced pressure. The residue was chromatographed on silica gel with benzene as an eluent, and then recrystallized from methanol to give spiro(Af-butylindolinonaphthooxazine) 33 (6.6 g, yield 51%). 

In the final stage, as depicted in Scheme 10, the BOC-protected compound 45 and the quinolone carboxylic acid 27 are heated in DMSO under tri-ethylamine, followed by deprotection of the terf-butoxycarbonyl group under acidic condition to afford the final product DQ-113 (26). 

Polymers containing pendant carbamate functional groups can be prepared by the reaction of phenyl isocyanate with poly(vinyl alcohol) in homogeneous dimethylsulfoxide solutions using a tri-ethylamine catalyst. These modified polymers are soluble in dimethyl sulfoxide, dimethylacetamide, dimethylformamide and formic acid but are insoluble in water, methanol and xylene. Above about 50% degree of substitution, the polymers are also soluble in acetic acid and butyrolactone. The modified polymers contain aromatic, C = 0, NH and CN bands in the infrared and show a diminished OH absorption. Similar results were noted in the NMR spectroscopy. These modified polymers show a lower specific and intrinsic viscosity in DMSO solutions than does the unmodified poly(vinyl alcohol) and this viscosity decreases as the degree of substitution increases. 

Another proton transfer studied by the E-jump technique in acetonitrile (42) is that between p-nitrophenol (AH) and tri-ethylamine (B). The extinction coefficients for each of the species in the following equilibrium have been measured by Kree-voy and Liang (3) ... 

Carbodiimide, diphenyl, 49, 70 Carbodiimides from ureas with tolu-enesulfonyl chloride and tri-ethylamine, 48, 86... 

Active methylene nitriles condense with o-substituted aryl and heteroaryl azides in a two-step process to give tricyclic triazolopyrimidines without isolation of the triazole intermediates <85BSB441, 87BSB587). 5-Azido-4-formyltriazoles (758) condense with dimethyl 3-oxopentanedioate and tri-ethylamine in ethanol to give 5-(triazol-l-yl)-4-formyltriazoles (759), which undergo cyclization to... 

Heating of 5-ethoxy-1,2,3,4-thiatriazolium tetrafluoroborate (161) with malononitrile and tri-ethylamine in acetonitrile solution gave crystalline l,2,3,4-thiatriazolium-5-dicyanomethylide (22) (Equation (13)) <79JCS(P1)744>. The structure is supported by spectral properties. The IR spectra show C=C (1500 cm ) and CN (2200 cm ) stretching vibrations and the mass spectra shows the correct molecular ions. A dipole moment of 8.8 D (R = Ph) was measured in benzene in good agreement with the proposed structure (22). 

DC030 Rhodes, B. B., and C. V. Hall. Effects of CPTA 2-(4-chlorophenyltio)-tri-ethylamine hydrochloride, temperature, and genotype on carotene synthesis in carrot leaves. Hortscience 1975 10 22. 

It has been recently described [55d) that aliphatic nitrile oxides can be formed in solution by treating an aliphatic a-nitro-hydrocarbon with phenylisocyanate in the presence of a catalytic amount of tri-ethylamine. Dehydration of the nitro compounds occurs with the con-committant formation of benzoylurea. From nitroethane, the reaction is formulated as follows ... 

Methyl-benzimidazol dimerisiert ebenfalls bei der Acylierung mit Benzoylchlorid und Tri-ethylamin als Base zu 3-Benzoyl-l-methyl-2-(l-methyl-2-benzimidazolyl)-2,3-dihydro-benzimid-azol (I 37% Schmp. 170-171°). Fuhrt man die Umsetzung statt bei 20° bei 140° (Ampulle) durch, so isoliert man 2-Benzoyl-1-methyl-benzimidazol (II 92% Schmp. 71 - 72°)417. Das Di-mere I laBt sich thermisch ebenfalls zu 2-Benzoyl-l-methyl-benzimidazol ( 61%) spalten. Die basische Oxidation des Dimeren I liefert dagegen fast quantitativ 1, Y-Dimethyl-2,2-bi-(benzimidazolyl) (III)417. 

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