N-alkyl anilines

N-Alkyl-aniline und Diphenylamin gehen mit 1,4-Dioxo- und mit 2,6-Dimethyl-l, 4-dioxo-cyclohexan eine saure-katalysierte Kondensation ein, die zu Alkyl-diaryl- bzw. zu Tri-aryl-aminen fuhrt diese Reaktion stellt insgesamt eine N-Arylierung dar2. 

Ortho substituted N-alkyl anilines are intermediates for an important class of pesticides. They can be synthesized by the reaction of the aniline with the appropriate alcohol ... 

Fig. 1. Plot of the yield of N-alkylated anilines AA (= YMEA.oc) versus heat of formation of the oxides of the promoting metals. Data from Table 1 and ref. 7.

N-Methylation of anilines.1 This system activates methanol for N-methyla-tion of anilines. RuCl2[P(C6H5)3]3 is more effective for N-methylation of N-alkyl-anilines. 

Commercial processes for obtaining the N-alkylated anilines are based on the reaction of aniline salts with alcohol in an autoclave at about 200°. A laboratory adaptation of this application of an alcohol as the alkylating... 

Fig. 5 Imine hydrogenation structures of MEA imine and (S)-N-alkylated aniline.

Table 2 N-alkylated anilines obtained by reductive alkylation.

The most common method for the formation of benzo-l-thia-2,4-diazines involves reaction of 2-aminoarenesulfon-amides with various one-carbon units (Section 9.05.9.2.3). Treatment of N-alkylated anilines with chlorosulfonyl isocyanate, followed by addition of a Lewis acid, results in 2//-benzo-l-thia-2,4-diazine-3(4//)-one 1,1-dioxides (Section 9.05.9.1.2) as does use of the Curtius rearrangement isocyanates produced at C-2 of the aryl ring that are then trapped by a sulfonamide function at C-1 (Section 9.05.9.1.3). Variants of intramolecular condensation reactions of 2-A -acyl-2-aminobenzenesulfonamides serve as a general route to 3-acyl or 3-alkyl ZH- and 4//-benzo-l-thia-2,4-diazine 1,1-dioxides (Section 9.05.9.1.3). 

Promoter - m6-tor n (14c) (promotor) A chemical substance that, in very small concentrating, increases the activity of a Catalyst. The promotor may itself be a weak catalyst. Examples in the curing of polyester resins are cobalt octoate used as the promoter with methyl ethyl ketone peroxide, and N-alkyl anilines used with benzoyl peroxide. 

E. L. Strebel, Eutectic Mixture of Para-Alkoxybenzylidene-Para-n-Alkyl Anilines, U.S. Patent 3,809.656, May 7. 1974. 

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