Phenyl aminosalicylate

After further cooling to about 60°C, 200 parts by volume of water and 500 parts by volume of ethyl acetate at 60°C are added, and the aqueous layer is separated. The excess of starting material may be recovered from the ethyl acetate. 

The aqueous portion is chilled in a cooling chamber at -10°C, whereupon the hydrochloride of 2-[N-(p-methylphenyl)-N-(m -hydroxyphenyl)-aminomethyl] -imidazoline crystallizes. 

Upon being concentrated and cooled the mother liquor yields a further quantity of the hydrochloride. The combined quantities of hydrochloride are treated with a small quantity of cold water, dried with care, and washed with ethyl acetate. The product is then crystallized from a mixture of alcohol and ethyl acetate, and there is obtained a hydrochloride melting at 239°-240°C. 

Miescher, K., Marxer, A. and Urech, E. U.S. Patent 2,503,059 April 4, 1950 assigned to Ciba Pharmaceutical Products, Inc. 

Therapeutic Function Antibacterial (Tuberculostatic) Chemical Name 4-Amino-2-hydroxybenzoic acid phenyl ester Common Name Fenamisal Structural Formula cc 

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One of the mainstays in the treatment of tuberculosis is paraaminosalicylic acid (PAS). It is not, however, a pleasant drug to take. Phenyl aminosalicylate (20) was synthesized from 4-nitrosalicylic acid (18) by esterification of its acid chloride with phenol to give 19, which is converted to the desired... 

Pharmacognosy, 466 Phenbutalol, 110 Phenearbamide, 97 Phenmetrazine, 261 Phenyl aminosalicylate,... 

Phensedyl, 932 Phensuximide, 889 Phentanyl, 617 Phentermine, 890 (metabolite), 732 Phentermine hydrochloride, 890 Phentolamine, 891 Phentolamine hydrochloride, 891 Phentolamine mesylate, 891 Phentolamine methanesulphonate, 891 Phenurone, 869 Phenyl aminosalicylate, 343 Phenyl hydrate, 884 Phenyl hydride, 380 Phenyl salicylate, 967 Phenylacetamide, 312 Phenylacetamidopenicillanic acid, 390 Phenylacetic acid mustard, 442 Phenylacetone, 350 Phenylacetylglutamine, 877 Phenylacetylurea, 869 Phenylalanine nitrogen mustard, 728 Phenylamine, 356... 

Phenyl Aminosalicylate, 4-A mino-2-hydroxybenz -oic acid phenyl ester p-aminosalicylic acid phenyl ester phenyl p-aminosallcylic acid p-aminosalol fenamisal Pbeo -yl PAS Pheny-PAS-Tebamin Tebamin, Tebanyl. C H,.-NO, mol wt 229.23. C 68.11%. H 4.84%. N6.ll%, O 20.94%. Description of properties Meyer, Antibiot. Ann. 1957-1958, 614. Prepd by Raney nickd reduction of the corresp nitre ester in ethyl acetate Friere. U.S. pat. 2,604,-488 (1952 to Rh6ne-Poulenc). 

Ph ester [133-11-9]. Phenyl aminosalicylate, BAN, USAN. FenanUsaly INN. p-Aminosalol. Temposil. NSC 40144 C13H11NO3 M 229.235 Tuberculostatic. Cryst. (2-propanol). Mp 153°. 

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