USRE13848E - The-main - Google Patents
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- Publication number
- USRE13848E USRE13848E US RE13848 E USRE13848 E US RE13848E
- Authority
- US
- United States
- Prior art keywords
- solution
- water
- grams
- diaminodioxyarsenobenzene
- acid
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000002253 acid Substances 0.000 description 26
- 235000019441 ethanol Nutrition 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 230000001264 neutralization Effects 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 229940017705 formaldehyde sulfoxylate Drugs 0.000 description 12
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000001187 sodium carbonate Substances 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- 229940001593 sodium carbonate Drugs 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- UKPBEPCQTDRZSE-UHFFFAOYSA-N cyclizine hydrochloride Chemical compound Cl.C1CN(C)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 UKPBEPCQTDRZSE-UHFFFAOYSA-N 0.000 description 6
- 229960004756 ethanol Drugs 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000003513 alkali Substances 0.000 description 4
- 150000001447 alkali salts Chemical class 0.000 description 4
- 125000004429 atoms Chemical group 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 101700056440 CCNI Proteins 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 241001237728 Precis Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229940037003 alum Drugs 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 230000001419 dependent Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000001184 potassium carbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001376 precipitating Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- 230000001131 transforming Effects 0.000 description 2
Definitions
- 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
- 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
- this new compound is:
- 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
- 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,
- 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.
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.
Family
ID=
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