32189-59-6

Upstream product

• 864131-95-3 N,N'-diphenylformamidine 
• 74-88-4 methyl iodide 
• 62-53-3 aniline 
• 93-61-8 N-methyl-N-phenylformamide 
• 36169-82-1 N-phenyl-formimidic acid methyl ester 
• 74-89-5 methylamine 
• 100-61-8 N-methylaniline 
• 103-70-8 Formanilid 
• 4949-93-3 1-methyl-1,3-diphenyl-thiourea 
• 63640-93-7 (N-methyl-N-phenyl)chloromethaniminium chloride 

Downstream Products

• 76529-16-3 3-methyl-2-[2-(N-methyl-anilino)-vinyl]-benzoxazolium; iodide 
• 76529-15-2 3-methyl-2-[2-(N-methyl-anilino)-vinyl]-benzothiazolium; iodide 

Relevant academic research and scientific papers

Method For Preparing Formamidines

A method for preparing formamidines of formula (I) in a single step by reducing ureas of formula (II) using silanes of formula (III), according to reaction (II)+(III)+(I) is provided. The present invention also provides a method for preparing insecticides

Transfer of amido groups from isolated rhodium(I) amides to alkenes and vinylarenes

The reaction of monomeric and dimeric rhodium(l) amido complexes with unactivated olefins to generate imines is reported. Transamination of {(PEt 3)2RhN(SiMePh2)2} (1a) or its -N(SiMe3)2 analogue 1b with p-toluidine gave the dimeric [(PEt3)2Rh(M-NHAr)]2 (Ar = p-tolyl) (2a) in 80% isolated yield. Reaction of 2a with PEt3 generated the monomeric (PEt3)3Rh(NHAr) (Ar = p-tolyl) (3a). PEt 3-ligated arylamides 2a and 3a reacted with styrene to transfer the amido group to the olefin and to form the ketimine Ph(Me)-C=N(p-tol) (4a) in 48-95% yields. The dinuclear amido hydride (PEt3)4Rh 2(μ-NHAr)(μ-H) (Ar = p-tolyl) (5a) was formed from reaction of 2a in 95% yield, and a mixture of this dimeric species and the (PEt 3)nRhH complexes with n = 3 and 4 was formed from reaction of 3a in a combined 75% yield. Propene reacted with 2a to give Me 2C=N(p-tol) (4b) and 5a in 90 and 57% yields. Propene also reacted with 3a to give 4b and 5a in 65 and 94% yields. Analogues of 2a and 3a with varied electronic properties also reacted with styrene to form the corresponding imines, and moderately faster rates were observed for reactions of electron-rich arylamides. Kinetic studies of the reaction of 3a with styrene were most consistent with formation of the imine by migratory insertion of olefin into the rhodium-amide bond to generate an aminoalkyl intermediate that undergoes β-hydrogen elimination to generate a rhodium hydride and an enamine that tautomerizes to the imine.

Amidines. Part 32. Influence of Substitution at the Amino Nitrogen Atom on the Sensitivity to Substitution at the Imino Nitrogen Atom. pKa Values of N1-Methyl-N1-phenylformamidines in Water-Ethanol Solutions

A series of new N1-methyl-N1-phenylformamidines (RN=CH-NMeC6H5, 13 compounds) containing variable substituents at the imino nitrogen atom has been synthesized.The pKa values of the compounds have been measured in four binary ethanol-water solvents and correlated with Hammett-type substituent constants, and with pKa values of the corresponding primary amines determined in the same solvents.It is shown that substitution at the amino nitrogen atom has considerable influence on the sensitivity of the amidino group to the polar effects of substituents at the iminonitrogen atom.The parameters for both types of regression depend on the solvent.The equation for prediction of the pKa values for trisubstituted amidines, enabling explanation of changes in the ρ values for substitution at one site caused by substitution at the other two sites, is derived.

A Convenient Synthesis of N-Substituted Formamidines by Desulfurization of the Corresponding Thioureas

N,N'-Di- and N,N,N'-trisubstituted thioureas were easily desulfurized by Raney nickel to yield the corresponding formamidines, while N-monosubstituted thioureas gave N,N'-disubstituted formamidines.