BENZANILIDE

Chemical Properties

greyish to yellow-green powder

Uses

Benzanilide is used to make dyes, active pharmaceutical ingredients and perfumes. It is also used to study the influence of beta-cyclodextrin on photorearrangement of acetanilide, benzanilide and ethyl phenyl carbonate. Further, it is used as an amide model compound to study the reaction between the amide and epoxy. In addition to this, it reacts with aryltriflates in the presence of palladium-based catalyst system to get N-(2,6-diarylbenzoyl)anilines.

Uses

manufacture of dyes and perfumes.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 187, 1987 DOI: 10.1002/jhet.5570240135
The Journal of Organic Chemistry, 20, p. 1482, 1955 DOI: 10.1021/jo01128a004
Tetrahedron Letters, 31, p. 1063, 1990 DOI: 10.1016/S0040-4039(00)94431-9

General Description

Benzanilide undergoes diarylation with aryl triflates or bromides in the presence of a palladium-based catalyst system to form corresponding N-(2,6-diarylbenzoyl)anilines. It is used in manufacture of dyes and perfumes.

Purification Methods

Crystallise benzanilide from pet ether (b 70-90o) using a Soxhlet extractor, and dry it overnight at 120o. Also crystallise it from EtOH. [Beilstein 12 IV 417.]