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)
-
Willi Kantlehner
,
Georg Ziegler
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
Graphical Abstract
![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)](/document/doi/10.5560/znb.2014-3269/asset/graphic/s69b0332.png)
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)
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
Articles in the same Issue
- Structural Diversity of Hydrogen-Bonded Networks of [Co(NH3)6]3+ Complex Cations and Acetylenedicarboxylic Acid Anions
- Different Structural Models of YB2C2 and GdB2C2 on the Basis of Single-Crystal X-Ray Data
- An Alternative Crystal Structure of Yb26B12O57 – X-Ray Structure Determination on Flux-synthesized Single Crystals
- Assembly of Zn(II) Coordination Polymers Based on Tetrachloroterephthalate and Dipyridyl-type Ligands
- The Silicides YT2Si2 (T =Co, Ni, Cu, Ru, Rh, Pd): A Systematic Study by 89Y Solid-state NMR Spectroscopy
- Mechanothermal Synthesis of SrSnO3
- A Dimeric Copper(II) Complex of Oxalate and Oxamide Dioxime Ligands: Synthesis, Crystal Structure, Thermal Stability, and Magnetic Properties
- Dicationic Methyl Complexes of the Rare-Earth Elements
- 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)
- Synthesis and Reactions of New Chiral Linear Carboxamides with an Incorporated Peptide Linkage Using Nalidixic Acid and Amino Acids as Starting Materials
- Sesquiterpenoids and Diterpenes from Chamaecyparis obtusa var. breviramea f. crippsii
- The New Ternary Silicide ErCo3Si2
- Crystal Structure and NMR Study of Tetrakis(acetonitrile)silver(I) Fluorosulfonate [Ag(CH3CN)4]+[SO3F]–
- Convenient Synthesis and Molecular Structure of PPN[RhCl2(CO)2] (PPN+ = Bis(triphenylphosphane)iminium)
Articles in the same Issue
- Structural Diversity of Hydrogen-Bonded Networks of [Co(NH3)6]3+ Complex Cations and Acetylenedicarboxylic Acid Anions
- Different Structural Models of YB2C2 and GdB2C2 on the Basis of Single-Crystal X-Ray Data
- An Alternative Crystal Structure of Yb26B12O57 – X-Ray Structure Determination on Flux-synthesized Single Crystals
- Assembly of Zn(II) Coordination Polymers Based on Tetrachloroterephthalate and Dipyridyl-type Ligands
- The Silicides YT2Si2 (T =Co, Ni, Cu, Ru, Rh, Pd): A Systematic Study by 89Y Solid-state NMR Spectroscopy
- Mechanothermal Synthesis of SrSnO3
- A Dimeric Copper(II) Complex of Oxalate and Oxamide Dioxime Ligands: Synthesis, Crystal Structure, Thermal Stability, and Magnetic Properties
- Dicationic Methyl Complexes of the Rare-Earth Elements
- 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)
- Synthesis and Reactions of New Chiral Linear Carboxamides with an Incorporated Peptide Linkage Using Nalidixic Acid and Amino Acids as Starting Materials
- Sesquiterpenoids and Diterpenes from Chamaecyparis obtusa var. breviramea f. crippsii
- The New Ternary Silicide ErCo3Si2
- Crystal Structure and NMR Study of Tetrakis(acetonitrile)silver(I) Fluorosulfonate [Ag(CH3CN)4]+[SO3F]–
- Convenient Synthesis and Molecular Structure of PPN[RhCl2(CO)2] (PPN+ = Bis(triphenylphosphane)iminium)
