N,N-Dimethylaniline → 2-(Bis(4-(dimethylamino)phenyl)methyl)-5-(dimethylamino)benzoic acid

Participants

Reaction Steps

A mixture of 38.0 ml of water, 17.4 g (0.1 mole) of 85.5 percent 4-dimethylaminobenzaldehyde, 6.0 g (0.1 mole) of urea, 12.6 g (0.1 mole) of N,N-dimethylaniline, 18.2 g (0.11 mole) of 3-dimethylaminobenzoic acid and 14.6 ml (0.273 mole) of concentrated sulfuric acid was maintained at a temperature in the range of 90° to 95° C. for approximately two and one-half hours with stirring. Slowly, 240.0 ml of water was added to the reaction mixture and the resulting mixture was stirred for approximately eight hours. The mixture was filtered to remove the insolubles and the filtrate was added with stirring to a solution of 30.0 ml of concentrated ammonium hydroxide dissolved in 150.0 ml of water. The pH of the resultant mixture was adjusted to 11.0 by gradually adding 21.6 g of 90 percent potassium hydroxide. After stirring approximately one-half hour, the mixture was filtered retaining both the filtercake and the filtrate. The filtrate was adjusted to a pH of approximately 4.8 by slowly adding glacial acetic acid. The solid which formed was collected by filtration, washed with water and dried in vacuo to obtain 4.1 g of 2-[bis(4-dimethylaminophenyl)]methyl-5-dimethylaminobenzoic acid (Formula II: Y=4--N(CH3)2 ; R=R1 =R2 =R3 =CH3), a solid.

Provenance & Evidence