1872.] 



for producing Amides and Nitriles. 



65 



by its lower melting-point. The isocompound fuses between 100° and 

 102°, whereas the normal butyramide melts at 115°. The boiling-point 

 is much the same for both*. 



Action of Valeric Acid on Potassium Sulphocyanate. 



In this instance, too, the reaction proceeds according to the two equa- 

 tions — 



HONS + C 5 H 9 O . OH= C 5 H 9 N + C0 2 + H 2 S, 

 HCNS + C 5 H 9 . OH= C 5 | N + COS. 



The separation and purification of the valeronitrile and valeramide are 

 similar in all respects to those employed for the corresponding compounds 

 in the butyric series. Yaleronitrile, already investigated by other chemists, 

 boils between 125° and 128°. By treatment with fuming nitric acid, it is 

 converted into a crystalline substance (perhaps C. H 8 (N0 2 )N), which I 

 have not as yet been able to examine further. 



Valeramide closely resembles isobutyramide. It is a w T hite crystalline 

 body of pleasant aromatic odour, recalling that of valerian-root : it is 

 soluble in water,- alcohol, and ether ; in the last-mentioned liquid much 

 more so than isobutyramide. From hot water it crystallizes in large 

 right-angled but very thin plates. Yaleramide fuses between 125° and 

 128°, and sublimes, in the same manner as isobutyramide, below its 

 boiling-point, which lies between 230° and 232°. It distils without de- 

 composition. 



Action of Benzoic Acid on Potassium Sulphocyanate. 



The aromatic acids of the C n H (2 , l _ 8) 2 series act in an analogous manner 

 on potassium sulphocyanate, with the difference, however, that here 

 nearly exclusively the nitrile is formed. The production of amide is so 

 insignificant as to be scarcely recognizable. The reaction with benzoic 

 acid takes place with particular facility, according to the equation 



HCNS + C 7 H 5 O . OH = C 7 H 5 N + C0 2 + H 2 S . 



2 mols. benzoic acid and 1 mol. potassium sulphocyanate (both hi a per- 

 fectly dry condition) are placed in a retort, to the mouth of which a long 

 wide tube is attached to serve as condenser. The apparatus thus 

 arranged is placed vertically, and heated either in a paraffin-bath or over 

 the naked flame. Both bodies melt, forming two layers, of which ben- 

 zoic acid is the lower one. At 190° the reaction commences, carbonic 

 anhydride and sulphuretted hydrogen behig evolved. At a higher tem- 

 perature the mixture enters into ebullition, and in about half an hour is 

 converted into a solid mass. The retort is now reversed, and the contents 



* It is remarkable that acetamide, butyramide, and isobutyramide all have nearly 

 the same boiling-point, namely 216°-220°. 



5? 2 



