Dipropyl aniline

Among tertiary aromatic amines, N,N-dimethyl-, A,A-diethyl-, and N,N-dipropyl-aniline can be nitrosated, but the reaction fails with A,iV-dibutyl-and A,A-diisopentyl-aniline.297... 

In addition to military uses, it should be noted that aromatic nitro compounds such as trifluralin (2,6-dinitro-A,A-dipropyl-4-(trifluoromethyl)aniline and dinoseb (2,4-dinitro-6-5 ec-butylphenol)... 

EXAMPLES methanamine (methylamine) Al, Al-dipropyl-l-propanaimne (tnpropylaumie) benzenamine (aniline)... 

A mixture of aniline (0.3 mole) and the requisite trialkyl phosphate (0.2 mole) is heated in a 500-ml flask for 2 h. The initial reaction is usually strongly exothermic, so that the temperature rises considerably. When the violent ebullition slackens the water-condenser is replaced by an air-condenser. The mixture is cooled to 50°, treated with a solution of sodium hydroxide (25 g) in water (100 ml), boiled for 1 h, and allowed to cool to room temperature in a beaker. The upper amine layer is separated from the precipitated sodium phosphate, and the latter is washed with ether. The amine and the ethereal solution are dried together over sodium sulfate, then freed from ether. The residue is set aside overnight with its own volume of acetic anhydride, then treated with a mixture of concentrated hydrochloric acid (20 ml) and water (30 ml), and shaken until all the amine has dissolved. The solution is then extracted with ether (two 30-ml portions), after which the amine is liberated by 25 % sodium hydroxide solution and taken up in ether. This extract is dried over sodium sulfate and distilled. The following are examples of yields of A A-dialkylanilines obtained by use of the appropriate trialkyl phosphate dimethyl 68%, diethyl 99%, dipropyl 78%, and dibutyl 79%. 

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