8330. Salicylanilide

Nomenclature

CAS number: 87-17-2
2-Hydroxy-N-phenylbenzamide; N-phenylsalicylamide; Salinidol (Doak).
C13H11NO2; mol wt 213.23.
C 73.23%, H 5.20%, N 6.57%, O 15.01%.

Description and references

Usually made by the reaction of salicylic acid with aniline in the presence of PCl3 at an elevated temp. Better yields are obtained by using an inert organic solvent such as toluene or carbon tetrachloride as a reaction diluent. Novel process using ion-exchange resins: Majewski, Skelly, US 3221051 (1965). Alternate process: Majewski et al., US 3231611 (1966 to Dow).

Chemical structure

Properties

Odorless leaflets. mp 135.8-136.2°. Slightly sol in water; freely sol in alcohol, ether, chloroform, benzene.

Caution

In concd form may cause irritation of skin, mucous membranes. See also Salicylic Acid.

Use

Anti-mildew, fungicide.

Therapeutic Category

Antifungal (topical).

Therapeutic Category (Veterinary)

Antifungal (topical).

Keywords

Antifungal (Synthetic)