USRE13848E - The-main - Google Patents

Description

UNITED STATES PATENT OFFICE.

GEOBG KORNDOBI'EB AND BAPTIST BlilUTEB, OF HOCHST ON-THEMAIN, GERMANY,

ASSIGHOBS TO FABBWEBKE VOB-H. MEISTEB LUCIUS & BBUNING, OI HOCHST-ON- THE-IAIN, GERMANY, A CORPORATION OF GEB IANY. v

DERIVATIVES OF DIAMINODIOXYARSENOBENZENE AND PROCESS OF MAKING SAME.

Specification of mm Letters 1 mm. Reissued De 15, 1914. I0 Drawing, Original 16. 11053300, alum February 1a, 191:, Serial m 892,081. Application 1dr reissue fled 28, 1914. Serial No. 858,750.

oxyarsenobenzene and Processes of Making Same, of which-the following a specificadi a solution of formaldehydesulfox'ylate e fo'r mula; CH,O.NaHSO,.2H,O to soqu so small an excess of alkali that the solutions can be regarded as being practically neutral. Such solutions retam the en-" tire therapeutical efliciency of the pure di- ,aminodioxyarsenobenzene, and owing to their neutral-solubility they present in their .therapeuticalapplication considerable advantages over the solutions from the, dihydrochlorid and thephenolate of diaminodioxyarsenobenzene. The quantit -of the .formaldehydesulfoxylate 'requi for obtainin clear solutions may be' varied within -widel1mits.' V

If a solution of :diaminodioxyarsenobe'nzene prepared in the above indicated manner is recipitated by means of hydrochloric aci preci itates result which theproperty 0 an acid. .Theyreadily dissolve in alkalis and ammonia, the solutions thus obtained showing a neutral reaction if an excess of alkali isavoided. The composition of these acids varies, dependent on whether the sulfoxylatehas reacted upon the diaminodioxyarsenobenzeneat ordinary temperatures, or at 60-70 C. I In the former'case an acid is produced comprising-only one--acid in, Germany,

general formula of the new compounds is 1 m? v a v nnx wherein X and' Y stand for the resi-' due known as methylenesulfin'ic acid replaced by hydrogen.v These acids orm bright yellowish powders, diflicultly soluble alkali salts are obtained'by dissolving these acids in the calculated quantity of caustic v soda .or'; potassium lye, aqueous ammonia or solutions of sodium-or potassium carbonate,

and precipitating the resulting solutions with alcohol -or acetone or evaporating them to dryness in a vacuum. The solidalkali salts also form yellowishpowders, readily soluble in water.

Example I: 25. grams of dihydrochlorid of diaminodioxyarsenobenzene are dissolved 1n 250 grams of water and to. this solution are} ad ed byrdrops, with stirring, 12.5

grams of formaldehydesulfoxylate dissolved in 125 grams of water. After one hour 80.

' coins. of a 10%,,solution of sodium carbonate is added,cwhereby a clear yellow solution is obtained which can be further diluted as desired and which nemainsclear when kep t.

Example II 25- grams of dih-ydro chlorid 'of diaminodioxyarsenobenzene are dissolved in 250 grams of water, andthere are then n added, with stirring, a solution of 25 grams of formaldehydesulfoxylate in 250 grams of water and after one hour ccms. oa 10% Q solution of sodium carbonate, To the clear solution thus obtained are added 100 ccms. of hydrochloric acid of 12% strength. The

group containing sulfur. this new compound is:

on AsCaH nacrnsona 21m,

I k i The formula of Example III: Fo transforming the acid obtained under Example 'IIinto its sodium salt,-2() grams of the acid are 'susp'ended in 70-80 grams of water, this suspension is dissolved by adding ccni's. of twice normal caustic soda lye, and the resulting solution is poured in a thin"stre'am .into 1000 ccms. of alcohol. Theprecipitate is filtered ofi, washed with alcohol and dried in .cacuo. The salt contains only one atom of sodium. ExamplelV: There is added toafinelydivided aqueous suspension of 21 grams of the base of diaminodioxyarsenobenzene, a

vsolution .of 25 grams of formaldehydesulfoxylate'in 60 grams of water, and'this',

mixture is gently heated on the water-bath until it is completely dissolved. The solution is precipitated by 25 ccms. of concentrated hydrochloric acid, and *the precipitated acid is further treated as indicated in Examples Hand III. The acid thus obtained contains two acid groups containin sulfur and itssodium salt two atoms 0 sodium.

Example V "parts by weight of hydro- I chlorid of -diaminodioxyarsenobenzene are dissolved in 200 parts of glycol and to this solution is added another solution of 31 parts of a formaldehydesulfoxylate in 50 parts of water. -After stirring 'for 5 minutes, a solution of sodium carbonate is added until thev solution'shows a neutral reaction. -Thus results a solution of 'diaminodioxyarsenobenzene of neutral reaction and ready for use, whi ch can'be diluted with water in any desired proportion without the solution becoming turbid. If this solution is run into large quantities of ethyl alco hol or a mixture-of ethyl alcohol and ether,

or acetone, a yellowish precipitate forms,

which is also readily soluble'inwater with neutral reaction. In the place of the glycol, in thisexa nple, other alcohols may be use vas solvents, for :instance methyl alcohol,

ethyl alcohol, glycerin or the like.

-. -Having now described our. invention,

what we claim is :1. The process of manufacturing new de- 'rivatives of .7 diaminodioxyarsenobenzene,

-' which have the formula which consists in reacting on diaminodioxyarsenobenzene with formaldehydesulfoxylate.

2. As new products, the derivatives of diaminodioxyarsenobenzene the radicals of which have the general formula:

theacid derivatives being yellowish powders, dii'licultly soluble in water, insoluble in alcohol, ether and acetone, dissolving in alkalis with formation of salts, these alkali salts being yellowish powders readily soluble in water.

3. Asnew products,'the"derivatives'of the diaininodioxyarsenobenzene, the radicals of the acid derivatives being yeuawishxpewders, ditiicultly soluble in water, insoluble in alcohol, ether and acetone and dissolving in alkalis with formation of salts constituting,- in theform'of'the sodium salt obtained with one equivalent of, caustic soda, a y'ellOWlSll powder readily soluble in water f with neutral reaction. v

-l. As a new product, the derivative of the diaminodioxyarsenobenzene, having the formula: r

being aiyellowish'powder readily soluble in water with neutral reaction, they corresponding :aoid being a. yellowish powder, diliicultly soluble inwateninsoluble in alcohol,

ether and acetoneand dissolving in alkalis with formation of a salt.'

In testimony whereof, we aiiix our signad tures in presence of two witnesses;

cEoRGKoRNDoRFER I Y P I T RT I'IIEB- Witnesses: r I .f I a O'rro RUPPELIUS,-

'BERNIIARD I zoEoKnR.