Phenylazobenzoyl Chloride

Phenylazobenzoyl chloride (azoyl chloride) has been prepared by the action of thionyl chloride on the acid.2 3 The method used is a modification of that of Ladenburg, Femholz, and Wallis.3... 

Alumina for esterification. A simple and rapid method of esterification which is particularly convenient for working on a scale of 20 mg. to 20 g. is as follows. An alcohol, for example ergosterol, is treated in benzene solution with a slight excess of benzoyl chloride or p-phenylazobenzoyl chloride and 2 equivalents of pyridine. When the reaction is complete, filtration through a small column of alumina (activity II, Woelm E. Merck) gives a solution of the desired ester in pyridine. After evaporation of the benzene, pyridine is removed by addition of toluene and evacuation on the steam bath. 

Alcohols p-Bromophenacyl bromide. 2,4-Dinitrobenzenesulfenyl chloride. 3,5-Dinitro-benzoyl chloride. o-Naphthylisocyanate. 4 -Nitroazobenzene.4<arboxylic acid chloride. p-Phenylazobenzoyl chloride. p-Phenylsulfonylbenzoyl chloride. p-Propionylisocyanate. 

N-Phenylanthranilic acid, 22, 5 Phenyl azide, 22, 96 -Phenylazobenzoic acid, 25, 86 -Phenylazobenzoyl chloride, 25, 87 Phenylbenzoyldiazomethane, 20, 48 a-Phenyl-0-benzoylpropionitrile, 27, 33 Phenyl cinnamate, 20, 77... 

From the phenol with p-phenylazobenzoyl chloride in pyridine... 

From the carbohydrate and azoyl chloride (p-phenylazobenzoyl chloride) in anhydrous pyridine For directions and examples see Cheronis, p 526,0 H Coleman, A G Farnham and A Miller, 7 Amer Chem Soc, 64,1501 (1942), G H Coleman and C M McClosky, 7 Amer Chem 5oc, 65, 1588 (1943)... 

In other experiments, poly(Lysine) was treated with p-phenylazobenzoic-N- hydroxy-succinimide ester (active esters method) in DMF/water solvent mixture. The reaction seems to be a suitable method to modify poly(Lysine) with organic reagents, and may be carried out both in organic and in aqueous solvents at acidic pH (Scheme 9) Finally, in one experiment, poly(Lysine) was acylated with p-phenylazobenzoyl chloride in DMF/water solvent mixture in the presence of excess MgO. 

The preparation of esters (76) of sugars with j -phenylazobenzoyl chloride is of interest mainly from the point of view of their isolation and separation from mixtures, the colors of the esters making it possible to separate them and detect them by column chromatography. 

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