Z. Naturforsch. 2014,
69b, 525 – 532
doi:10.5560/ZNB.2014-3270
Orthoamides and Iminiumsalts LXXXIV [1]. The Synthesis of Strong Formylating Reagents on a Large Preparative Scale: Tris(chloromethyl)amine
Orthoamide und Iminiumsalze, LXXXIV [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: Tris(dichlormethyl)amin
Willi
Kantlehner1,2,
Georg
Ziegler1,
Oliver
Scherr1,
Michael
Csiesielski1,
Alain
Goeppert1,
Markus
Wezstein1,
Jochen
Mezger1,
Ivo C.
Ivanov1,3, and
Sylvia
Leonhardt1
1 Fakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstr. 1, D-73430 Aalen, Germany
2 Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
3 Department of Organic Chemistry, Faculty of Pharmacy, Medical University of Sofia, Dunav 2, BG-1000 Sofia, Bulgarien
Received October 3, 2013 / published online May 7, 2014
Professor Branko Stanovnik zum 75. Geburtstag gewidmet
Tris(chloromethyl)amine (4) can be prepared by chloromethylation of urotropin with paraformaldehyde or 1,3,5-trioxane and ethyl-trichlorosilane in good yields. Photochlorination of tris(chloromethyl)amine affords tris(dichloromethyl)amine (2). Both reactions can be performed on large scale.
Key words: Preparation, Large Scale, Formylating Reagents, Tris(chloromethyl)amine, Tris(dichloromethyl)amine, Photochlorination