Orthoamide und Iminiumsalze, LXXXIII [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: Triformamid (Triformylamin) / Orthoamides and Iminium Salts LXXXIII [1]. The Synthesis of Strong Formylating Reagents on Large Preparative Scale: Triformamide (Triformylamine)

Abstract

The preparation of sodium diformamide (7) from formamide and sodium methanolate under azeotropic removal of methanol with cyclohexane, or from formamide and sodium ethanolate in ethanol, is described. Diformamide (8) can be prepared by treatment of sodium diformamide (7) with formic acid. Triformamide (triformylamine) (1) is formed in the reaction of sodium diformamide with inorganic acid halides such as SOCl2, SO2Cl2 or PCl3 in acetonitrile at low temperatures. Triformamide (1) can be prepared on a large scale by the action of methanesulfonyl chloride on finely powdered sodium diformamide (7) in acetonitrile. Tris(diformylamino)methane (4) can be formed as a side product. A procedure was developed for the large-scale preparation of N;N-diformylacetamide (6) from sodium diformamide and acetyl chloride. Triformamide (1) can be prepared from N;Ndiformylacetamide (6) and diformamide with good yields

Praziquantel – 50 Years of Research

“…To be competitive, Valiant decided to introduce the Shing‐Poong process. In collaboration with Merck the following new process to produce the aminoacetal 15 from sodium diformylimide 12 [40] was proposed and subsequently implemented by Valiant (Scheme 4).…”