Bei dieser Reaktion wird zunächst allgemein ein Pinner-Salz (4) hergestellt. Dadurch entsteht ein Ammonium mit Hydroxygruppe 6.

[4.0 g, 94%], [Patent Reference: WO2014149164, page 234, (23.7 MB)], A solution of the SM (180 mg, 0.53 mmol) in MeOH (50 mL) and H2SO4 (2 mL) was refluxed for 16 h. After concentration, the residue was dissolved in DCM (100 mL) and adjusted to pH = 8 with 3N NaOH.

The most common alcohols employed are MeOH and EtOH, but many primary and secondary alcohols have been used.

Diese Seite wurde zuletzt am 24. Learn more. A less frequently used pyrolysis leads to carboxamides (Scheme€3) [3-5]. Das sogenannte Pinner-Salz kann mit unterschiedlichen Nucleophilen weiterreagieren.

Gibt man ein primäres oder sekundäres Amin zu einem Pinner-Salz (4), so lagert sich das Stickstoffteilchen des Amins am Kohlenstoff des Pinner-Salzes an.

The transformation of nitriles into imidines or their salts by the treatment of nitriles with an excess of strong acid and one equivalent of alcohol followed by an excess of ammonia or amines is generally known as the Pinner synthesis, or Pinner reaction. Synthesis of Amidines The two approaches can be complementary, with nitriles which are unreactive under acid conditions often giving better results in the presence of base, and vice versa. Treatment of the nitrile with gaseous HCl in a mixture of anhydrous This reaction is useful for the preparation of imidines. [2][3][4] The Pinner reaction refers to the acid catalysed reaction of a nitrile with an alcohol to form an imino ester salt (alkyl imidate salt); this is sometimes referred to as a Pinner salt. Chem., 2010, Cl NH2.HCl COOH

The high toxicity and the laborious handling of gaseous hydrogen chloride are further drawbacks of this reaction. Working off-campus?

Pinner Reaction.

Besides ethanol and methanol, other alcohols have also been found suitable for this reaction. Orthoesters can be prepared by the Pinner reaction, in which nitriles react with alcohols under acid catalysis: RCN + 3 R′OH → RC(OR′) 3 + NH 3 Reactions Hydrolysis. To a solution of the SM (0.2 g, 0.3 mmol) in EtOH (5 mL) was added conc.

Die Pinner-Reaktion ist eine Namensreaktion der organische Chemie.

Click on the reaction arrow to visit the page. Außerdem spaltet sich Ammoniak aus dem Molekül ab. HCl (5 mL). HCl (5 mL).

B. P. Mundy, M. G. Ellerd, F. G. Favaloro: https://de.wikipedia.org/w/index.php?title=Pinner-Reaktion&oldid=201258175, „Creative Commons Attribution/Share Alike“. Versetzt man das Pinner-Salz mit Wasser, so kann man daraus einen Carbonsäureester gewinnen.

The source code for the WIKI 2 extension is being checked by specialists of the Mozilla Foundation, Google, and Apple. 1) Kurti, L.; Czako, B.; Strategic Applications of Named Reactions in Organic Synthesis.

To a solution of the SM (0.2 g, 0.3 mmol) in EtOH (5 mL) was added conc. Org. Die Aktivierung von Nitrilen erfolgt unter wasserfreien … Dieses Salz kann dann weiter verarbeitet werden durch Umsetzung mit weiteren Reagenzien. aliphatic, aromatic, and heteroaromatic nitriles). Dieses nimmt das Wasserstoff-Ion auf, welches bei der Deprotonierung frei wurde.

The two approaches can be complementary, with nitriles which are unreactive under acid conditions often giving better results in the presence of base, and vice versa. Dadurch bildet sich das Molekül 8 aus. Recent Literature. Berichte der deutschen chemischen Gesellschaft, "Ueber die Umwandlung der Nitrile in Imide", With hydrogen sulfide to form a thionoester. If the starting substrate contains an ester, a possible side reaction is ammonolysis; this is especially prevalent when aqueous ammonia is used ( Equation (8) ) < 54CLY1210 >. Dieses wird aus einem Nitril und einem Alkohol unter Einwirkung von Salzsäure hergestellt und liefert das Pinner-Salz, das Hydrochlorid eines Imidats. The resulting material was stirred in H2O for 15 min, extracted with EtOAc, dried (Na2SO4), and concentrated in vacuo to provide the product as a yellow liquid. The mixture was quenched with H2O (50 mL), basified with 10% NaOH up to pH 9, and extracted with EtOAc (2 x 30 mL) The combined organics were washed with H2O (50 mL), brine (50 mL), dried (Na2SO4), and concentrated.

Im Anschluss findet ein intramolekularer Protonentransfer statt und es bildet sich das Kation des sogenannten Pinner-Salz 4 (mit Chlorid als Anion).

Learn about our remote access options. in one go. It will enhance any encyclopedic page you visit with the magic of the WIKI 2 technology. The reaction was kept standing for 16 h, after which time the reaction mixture was concentrated in vacuo. but a poor nucleophile would be difficult to protonate and hence would be expected to react more readily under basic rather than acidic conditions. An efficient method for the conversion of aromatic and aliphatic nitriles to the corresponding N-tert-butyl amides: a modified Ritter reaction K. L. Reddy, Tetrahedron Lett., 2003, 44, 1453-1455. Preparation and Utility of Trihaloethyl Imidates: Useful Reagents for the Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters.

Versetzt man das Pinner-Salz mit Wasser, so kann man daraus einen Carbonsäureester gewinnen. You could also do it yourself at any point in time. Juni 2020 um 09:06 Uhr bearbeitet. The Pinner Bei dieser Reaktion wird zunächst allgemein ein Pinner-Salz (4) hergestellt. Please check your email for instructions on resetting your password.

[118 mg, 60%], [Patent Reference: WO2016011390, page 201, (20.2 MB)]. Lage… Die Elektronen der C-N-Dreifachbindung des Nitrils lagern sich um und es bildet sich die Iminogruppe 3 aus. derivatives and methanol according to the sequence of steps in Scheme 7.

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