Reaction #1668093

Reaction equation

2-chloro-5-nitroaniline

2-chloro-5-tetradecanoylaniline

β,β-diethoxyacrylic acid ethyl ester

→

β-(2-chloro-5-tetradecanoylaminoanilino)-β-ethoxyacrylic acid ethyl ester

Conditions

Workup

1. 1
   Otheras Method (a) of Synthesis Example 1

Procedure

Using the same procedure as Method (a) of Synthesis Example 1, in place of 2-chloro-5-nitroaniline, 152 g of 2-chloro-5-tetradecanoylaniline was reacted with 94 g of β,β-diethoxyacrylic acid ethyl ester at 130°-150°C for 3 hours to give β-(2-chloro-5-tetradecanoylaminoanilino)-β-ethoxyacrylic acid ethyl ester. The product was, without being isolated and purified, mixed with 106 g of 2,4,6-trichlorophenylhydrazine and 500 ml of acetic acid and the mixture was refluxed for 2 hours. After distilling off the acetic acid from the reaction product mixture under a reduced pressure, a mixture of 300 ml of acetonitrile and 300 ml of ethanol was added to the reaction product followed by heating to dissolve the product therein and the solution was, then, allowed to cool to form precipitates, which were collected by filtration and recrystallized from a mixture of 150 ml of acetonitrile and 150 ml of ethanol to give 87 g of the desired product having a melting point of 115°-118°C.

Source