Year: 1891

page_text: Date of Application, 19th May, 1891
Complete Specification Left, 16th Feb., 1892-Accepted, 19th Mar., 1892
To a solution of 300 grammes of phenacetin in 600 grammes of alcohol I have
added a solution of 300 grammes of iodine in 600 grammes of hydrochloric acid of
The quantity
50 per cent., and have again obtained the same new compound.
obtained was 530 grammes.
The product when dried, is a crystalline powder, of chocolate colour, and melts
at 130° C. It is easily soluble in glacial acetic acid, more sparingly in acetic acid
of 50 per
cent. strength, moderately soluble in alcohol, sparingly soluble in benzene
and chloroform and almost insoluble in water. The new compound gives off iodine.
with great facility. On being heated, and especially on boiling with the said
solvents, it is slowly decomposed while giving off iodine.
On prolonged boiling with water the said iodine derivative, also called "iodo-
phenin," gives off iodine vapours, until there remains pure phenacetin.
Iodo-phenin is energetically split up into iodine and phenacetin, by the action of
alkalies or of sodium sulphate.
For recrystallizing iode-phenin, I employ preferably glacial acetic acid, which
produces large oblong crystals with a greenish-red lustre. Somewhat smaller
crystals are obtained by recrystallization from chloroform mixed with 5 to 10 per cent.
of alcohol. According to analysis the new compound seems to contain 2 molecules
of phenacetin for 3 atoms of iodine. In conclusion the essential feature of my inven-
tion may be said to consist in producing an iodine derivative of phenacetin, having
the qualities described, by adding to a solution of phenacetin, a solution of iodine
in the presence of a free acid.
10 of Mov 1901
FAIRFAX & WETTER,
Agents.

page_text: AAMTLE.
To a solution of 300 grammes of phenacetin in 600 grammes of alcohol, I have
added a solution of 300 grammes of iodine in 600 grammes of hydriodic acid (of
50 per cent.), and have again obtained the same new compound. The quantity
obtained was 530 grammes.
The product, when dried, is a crystalline powder, of chocolate colour, and melts
at 130° C., while undergoing decomposition. It is easily soluble in glacial acetic
acid, more sparingly in acetic acid of 50 per cent. strength, moderately soluble in
alcohol, sparingly soluble in benzene and chloroform and almost insoluble in water.
The new compound contains iodine and is remarkable for the facility with which it
gives off this substance. On being heated, and especially on boiling with the said
solvents, it is slowly decomposed, while giving off iodine.
On prolonged boiling with water, the said iodine derivative, also called "iodo-
phenin," gives off iodine vapours, until there remains pure phenacetin.
The latter has been identified by its melting point and the formation of amido-
phenetol after boiling with hydrochloric acid and treatment with soda-solution.
Alkalies and sodium thiosulphate act very energetically on the new body by
splitting it up iuto iodine and phenacetin; even slightly alkaline liquids, such as
discharges from wounds, decompose the compound gradually, so as to give off
iodine. This great facility with which the, new compound yields iodine, seems to
indicate, that it is produced by the addition of iodine to the nitrogen of the
phenacetin.
For recrystallizing iodo-phenin, I employ preferably glacial acetic acid, which
produces large oblong crystals with greenish-red lustre. Somewhat smaller
crystals are obtained by recrystallization from chloroform mixed with 5 to
10 per cent. of alcohol. According to analysis, the new compound seems to
contain 2 molecules of phenacetin for 3 atoms of iodine.

page_text: Its empyrical formula is therefore ;
CH,N,O,I,
25
The percentage of iodine calculated from this formula is 51.55, and according to
experiments it is 50-3 or 50-8 or 51.4.
The new compound, "iodo-phenin," is applicable for therapeutic purposes on
account of the facility with which it gives off iodine.
Having now particularly described and ascertained the nature of the said inven-
tion, and in what manner the same is to be performed, I declare that what I
claim is;-
The production or manufacture of an iodine derivative of phenacetin having the
properties specified, by treating a solution of phenacetin with a solution of iodine
in the presence of free acids.
Doted this 16th dov at Habruary QOD
Doted this 16th d
h day. ICabrio ru
L. F. RIEDEL,
By Fairfax & Wetter,
433, Strand, London, Agents.
L. F. RIEDEL,
By Fairfax & Wetter,
433, Strand, London, Agents.