14068-24-7

Upstream product

• 32119-55-4 2-(Methyl-p-tolyl-amino)-1-phenyl-ethanone 
• 50-00-0 formaldehyd 
• 4693-68-9 N,N'-di-p-tolylethylenediamine 

Downstream Products

• 101587-54-6 N-(2-p-toluidino-ethyl)-N-p-tolyl-formamide 

Relevant academic research and scientific papers

Synthesis of substituted 1H-4,5-dihydroimidazolium salts by dehydrogenation of imidazolidines

A study is presented on the scope of the method to obtain 1H-4,5-dihydroimidazolium salts 3 by dehydrogenation of 1,3-di and 1,2,3-trisubstituted imidazolidines 2. Of the dehydrogenating agents used, N-bromoacetamide leads to the best results, providing a

Light-induced Reactions of 2-(N-Alkyl-N-arylamino)acetophenones and Related Amino-ketones: Formation of 1,3-Diarylazetidin-3-ols

On irradiation in ether, 2-(N-methylanilino)acetophenones, Ar1NMe-CH2COAr2 (Ar1,Ar2=Ph,Ph; Ph,p-MeO-C6H4; Ph,p-Ph-C6H4; p-Cl-C6H4,Ph; p-MeO-C6H4,Ph; and p-Me-C6H4,Ph), underwent type II cyclisation to isomeric 1,3-diarylazetidin-3-ols.A minor photoproduct was one of the two expected type II fission products, the corresponding acetophenone Ar2COMe.The second type II fission product, imine Ar1N=CH2, was not detected, but in three cases a 1,3-diarylimidazolidine, probably derived from this imine, was isolated.Similar results were obtained on irradiation of the related amino-ketones, 2-(N-methylanilino)-2'-acetonaphthone and 2-(N-methylanilino)-1-tetralone.Direct fission of the C-2-N bond occured on irradiation of 2-(N-methylanilino)indan-1-one and 2,2-dimethyl-2-(N-methylanilino)acetophenone. 2-(N-Alkylanilino)acetophenones, PhNR-CH2COPh (R=Et, Me2CH, and PHCH2), yielded complex mixtures on irradiation.

Transmission of substituent effects through the nitrogen-silicon-nitrogen system

Transmission of substituent effects as determined by nmr chemical shifts is used to test the hypothesis of (p → d)-π bonding in the N-Si-N system. Unsymmetrically substituted N,N′-p- and -m-diphenylimidazolidines and -diphenylsilaimidazolidines were chosen for this study as such molecules satisfy the requirement that the substituents be held relatively far from one another on the scale of molecular dimensions, thus minimizing inductive and direct electrostatic field effects as well as magnetic anisotropy which might alter the chemical shift of the protons under examination. Studies were carried out in mixtures of the compound with the N-p-nitrophenyl,N′-p-dimethylaminophenylimidazolidine as a reference in each case (Chemical Equation Presented) [M = C, Si; X= p-NO2, p-OCH3, p-Cl, m-NO2, and p-N(CH3)2] and chemical shifts extrapolated to infinite dilution in chloroform to eliminate bulk magnetic susceptibility effects. Chemical shift differences in the dimethylamino group could be measured to better than ± 0.1 cps in this way. Transmission across analogous N,N′-diphenylethylenediamines is negligible. Shifts for a variety of organic N,N′-substituted diphenylimidazolidines are shown to correlate with the Hammett σ constant for each substituent. Shifts for the analogous silicon series are found to fall on the same linear plot against the Hammett σ constant for each substituent. Consequences of this finding on the possibility for (p → d)-π interactions in the N-Si-N system are discussed.