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Патент USA US2137237

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2,137,237
Patented Nov. 22, 1938'
K;
PATENT orrica
2,137,237
' ]_ JPKREGYIPIT‘ATION 0F NEOARSPHENAIYHNE
.
"
.
‘
AND
SULPHARSPHENAMINE
>
»
Walter G. Christiansen, Glen Ridge, N. J., and
AlfredErJurist, Brooklyn, N. Y., assignors to
E. R.._ Squibb & Sons, New York, N. Y., a cor
poration of New York
No Drawing. Application January 12, 1937,
Serial No. 120,240'
10 Claims.
.
'
(01. 260-444) V
Thisinvention relates to the preparation of
arseno-benze'nef' ideriv'atives, particularly com
pounds of the c'lass‘bons‘isting of sulpharsphen
amine (disodium-3,3'-diamino-4,4'-dihydroxyar
senobenzene-N,N'-dimethylenesulphonate) and
neoarsphenamine (sodium-3,3’-diamino-4,4'-di—
hydroxyarsenobenzene methanol sulphoxylate) .
sulpharsphenamine and neoarsphenamine have
heretofore been prepared by processes involving
to litmus." This alkaline solution is then ?ltered
and the ?ltrate poured into ten volumes of cold,
dry isopropanol with constant stirring. The yel
low precipitate, when collected on a Buchner
funnel, washed with isopropanol, and dried in a 5
vacuum over anhydrous calcium sulphate, gives
' neoarsphenamine in the desired form.
15 g. of arsphenamine baseis dissolved at room
temperature in a mixture of‘ 185 cc. of water, 27,
10 precipitationthereof from aqueous, often alcohol
cc. of methanol, ethanol, or isopropanol, and 6.9 ,10 '
or mixtures of ethanol and ether. However, the
precipitates so- obtained are usually very ?ne pow
ders which settle out slowly; which, when desic
15 cated and ampuled, adhere to the inner Walls of
ous solution). After stirring about a minute, 22.5
cc. of sodium bisulp-hite (37% aqueous solution)
is added; and after stirring for an additional
containing, solutions bytreatment with ethanol
the ampules; and which, when contained in
evacuated ampules, are to some extent blown out
by inrushing ‘air upon rupture of the seal.
It is the object of this invention to provide a
20 method of preparing compounds of the class con
sisting of sulpharsphenamine and neoarsphena
mine in the form of coarse, free-?owing, gran
ules which do not adhere to ampule walls and
are not readily blown out.
In the practice of this invention, compounds
25
of the class consisting of sulpharsphenamine and
neoarsphenamine are precipitated from their
aqueous solutions (which may contain an alcohol)
with isopropanol; and—in order that clear, in
30 stead of hazy, aqueous solutions may be se
cured-the precipitates are preferably dried with
anhydrous calcium sulphate under reduced pres
sure. It is advantageous to carry out the precipi
tation anaerically, as by ?ooding the reaction
vessels with nitrogen or carbon dioxide.
35
Examples
'
A solution of 8.1 g. of arsphenamine in 100 cc.
of water is treated with 5.7 g. to 9.6 g. (three to
40 ?ve molecular equivalents) of sodium formalde
45
cc. of hydrochloric acid; and the solution is
treated with 3.61:0. of formaldehyde (37% aque
?ve minutes, a ‘second and equal portion of so
dium bisulphite solution is added. Agitation for
another twenty minutes follows, and then ?ltra
tion; and the ?ltrate is poured‘ into 3.5 volumes
of cold, dry isopropanol with constant stirring. 20
The precipitate, upon being ?ltered off, washed
with‘ isopropan'ohand dried over anhydrous cal
cium sulfate in a vacuum, yields sulpharsphen
amine in the desired form.
It is to be understood that the examples given
herein are merely illustrative and not limitative
of this invention, which may be variously other
wise embodied-as with respect to the alcohol
used in the reaction mixture, the proportions of
_ the reactants, and ‘the conditions and procedures 30
employed—within the scope of the. appended
claims.
We claim:
1. In the preparation of compounds of the
class consisting of sulpharsphenamine and neo 35
arsphenamine, the step. of precipitating said com
pounds from their aqueous solutions by means
of substantially dry isopropanol.
2. In the preparation of compounds. of the
class consisting of sulpharsphenamine and neo
hyde bisulphite in aqueous solution, while being
arsphenamine, the step of precipitating said com- ,
constantly stirred. When the reaction is com
plete, the mixture is ?ltered and the clear ?ltrate
is poured, with agitation, into ?ve volumes of
pounds from their lower-saturated-aliphatic-al
cold, dry isopropanol.
3. In the preparation of compounds of the
.class consisting of sulpharsphenamine and neo
arsphenamine, the step of precipitating said com
pounds from their methanol-containing aqueous
Collecting the precipi
tate on a Buchner funnel, washing with isopro
panol, and drying the ?lter cake over anhydrous
calcium sulphate in a vacuum, yields, sulphars
phenamine in the desired form.
A solution of 44.0 g. of arsphenamine in 180 cc.
of methanol is treated at room temperature with
cohol-containing aqueous solutions by means of
substantially dry isopropanol.
solutions by means ‘of substantially dry isopro
panol.
.
4. In the preparation of compounds of the '
solved in 50 cc. of water. Any precipitate formed ' class consisting of sulpharsphenamine and neo
32 g. of sodium formaldehyde sulphoxylate dis
is redissolved by adding sodium carbonate to the arsphenamine the step of precipitating said com- '
55 reaction mixture until the latter is faintly alkaline . pounds from their ethanol-containing aqueous
2
2,137,237
solutions by means of substantially dry isopro
panol.
,
class consisting of sulpharsphenamine and neo
arsphenamine, the steps of precipitating said
5. In the preparation of compounds of the class _ compounds from their methanol-containing aque
consisting of sulpharsphenamine and neoarsphen
ous solutions by means of substantially dryiso
amine, the step of precipitating said compounds Vpropanol and drying the precipitates with anhy
from their isopropanol-containing aqueous solu
drous calcium sulphate in a vacuum.
tions by means of substantially dry isopropanol.
9. In the preparation of compounds of the
6. In the preparation of compounds of the class consisting of sulpharsphenamine and neo
class consisting of sulpharsphenamine and neo
arsphenamine, the steps of precipitating said
arsphenamine, the steps of precipitating said
compounds from their aqueous solutions by means
of substantially dry isopropanol and drying the
precipitate with anhydrous calcium sulphate un
der reduced pressure.
15
7. In the preparation of compounds of the
class consisting of sulpharsphenamine and neo
arsphenamine, the steps of precipitating said
compounds from their lower-saturated-aliphatic
alcohol-containing aqueous solutions by means of
20
substantially dry isopropanol and drying the
compounds from their ethanol-containing aque 10
ous solutions by means of substantially dry iso
prdpanol and drying the precipitates with an
hydrous calcium sulphate in a vacuum.
10. In the preparation of compounds of the
class consisting of sulpharsphenamine and neo- 15
arsphenamine, the steps of precipitating said
compounds from their isopropanol-containing
aqueous solutions by means of substantially dry
isopropanol and drying the precipitates with an
hydrous calcium sulphate in a vacuum.
precipitate with anhydrous calcium sulphate un
der reduced pressure.
.
8. In the preparation of compounds of the
WALTER G. CHRISTIANSEN.
ALFRED E. JURIST.
20
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