PHENACETIN. 33 



PHENACETIN PATENTS AND TRADE-MARKS. 



UNITKD STATKS 1* \TI.\T OKFJCK. 



Oskar Hinsberg, of Barmen, Assignor to the Farbenfabriken, Vormals Fr. Bayer fe Co., of Elberfeld, 



Germany. 



I'llKN ACKTINK. 



$1 unification forming part of letters patent No. 400086, dated March 26, 1889. Applica- 

 tion filed June 29, 1888. Serial Xo. 278593. (Specimens) 



To all whom it may concern: 



Be it known that I, Oskar Hinsberg, a citizen of the Km pi re of Germany, residing 

 at Barmen, in the said Empire, have invented a Useful Improvement in the Manu- 

 facture of a New Pharmaceutical Product, of which the following is a specification. 



My invention relates to the production of a new pharmaceutical product, a new 

 antipyretic and anti neuralgic, obtained by reducing nitrophenetole and melting the 

 phenetidinchlorhydrate thus formed with dried sodium acetate and acetic acid. 



In carrying out my process practically I proceed as follows: Fifty kilon of the 

 potassium salt of paranitrophenole are mixed with three hundred kilos of alcohol, 

 adding forty kilos of bromaethyl. The mixture is heated in an autoclave at a pres- 

 sure of three to four atmospheres during about eight hours. At this time the reac- 

 tion is finishe 1, whereby paranitrophenetole is obtained according to the following 

 equations: 



/ONa /OC 2 H 5 



C 6 H 4 -f-C 2 H 5 Br=C 6 H 4 +BrNa 

 \ NO \ NO, 



In order to separate the mononitrophenole, which has not taken any part in the 

 process, from the ether recently formed, the solution is treated with steam. By this 

 operation the ether distills, leaving behind the paramononitrophenole. 



For the reduction of the paranitrophenetole forty kilos of this ether are mixed 

 with sixty kilos of muriatic acid and sixty kilos of water. To this mixture are 

 gradually added, at a temperature of 70 centigrade, twenty-five kilos of iron tilings, 

 the whole being stirred continually. As soon as the ether is entirely reduced, para- 

 amidophenetole is obtained, as explained by the following equation: 



XOC,H 5 /OC 2 H 5 

 C 6 H 4 +H 6 =:C 6 H 4 +2H 2 

 \NO 2 \NH, 



The solution obtained in this manner is saturated with chalk diluted with water, 

 and for the purification of the amido compound treated with steam the distillate is 

 absorbed in w r ater acidulated by muriatic acid. The muriatic salt of the para- 

 amidophenetole crystallizes in white leaves. Fifty kilos of this product are melted 

 with one molecule of melted acetate of sodium and twenty four kilos of glacial acetic 

 acid. The melted mass is repeatedly boiled with water and the new ninnoacetyl- 

 paramidophenetole obtained from the filterates after cooling. It has the fol lowing 

 chemical formula: 



/XH (C,H 3 0) 

 Para C 6 H 4 =C 10 O 2 H 15 N 





and is obtained according to the following equations: 



Para C 6 H 4 +CH3COOH=C 6 H 4 +H 2 0' 

 \OCW 4 ' 



13528 No. 8004 - 3 



