DE940896C - Process for the production of sulfur-containing mercury compounds - Google Patents
Process for the production of sulfur-containing mercury compoundsInfo
- Publication number
- DE940896C DE940896C DEF8648A DEF0008648A DE940896C DE 940896 C DE940896 C DE 940896C DE F8648 A DEF8648 A DE F8648A DE F0008648 A DEF0008648 A DE F0008648A DE 940896 C DE940896 C DE 940896C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- oxymercuri
- carboxy
- sulfur
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- 150000002731 mercury compounds Chemical class 0.000 title claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims description 7
- 229910052717 sulfur Inorganic materials 0.000 title claims description 7
- 239000011593 sulfur Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 150000003839 salts Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- -1 β-carboxy-propionylamino Chemical group 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- PCYGQWDOXVVKLM-UHFFFAOYSA-N 2-sulfanylidene-3h-1,3-benzoxazole-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC(=S)OC2=C1 PCYGQWDOXVVKLM-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- DDVASFXNOCRVCR-UHFFFAOYSA-N 2-sulfanyl-3H-1,3-benzoxazole-2-carboxylic acid Chemical compound C1=CC=C2C(=C1)NC(O2)(C(=O)O)S DDVASFXNOCRVCR-UHFFFAOYSA-N 0.000 description 1
- IILRWDAJGJROQW-UHFFFAOYSA-N 2-sulfanyl-3h-1,3-benzothiazole-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)(S)NC2=C1 IILRWDAJGJROQW-UHFFFAOYSA-N 0.000 description 1
- IQCOJHLXUZMKBM-UHFFFAOYSA-N 2-sulfanylbenzimidazole-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)(S)N=C21 IQCOJHLXUZMKBM-UHFFFAOYSA-N 0.000 description 1
- DCRZVUIGGYMOBI-UHFFFAOYSA-N 2-sulfanylidene-1,3-dihydrobenzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC(=S)NC2=C1 DCRZVUIGGYMOBI-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000005825 oxyethoxy group Chemical group [H]C([H])(O[*:1])C([H])([H])O[*:2] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
- C07F3/14—Heterocyclic substances containing mercury
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von schwefelhaltigen Quecksilberverbindungen Die bisher bekannten diuretisch wirksamen Quecksilberverbindungen, die fast ausnahmslos Allylamide aliphatischer, aromatischer, hydroaromatischer oder heterocyclischer Carbonsäuren darstellen, zeigen als Natriumsalze durchweg alkalische Reaktion und sind nur mit x, 3-Dimethylxanthin (Theophyllin) versetzt für die Praxis brauchbar.Process for the production of sulfur-containing mercury compounds The previously known diuretically active mercury compounds, almost without exception Allylamides of aliphatic, aromatic, hydroaromatic or heterocyclic Represent carboxylic acids, show an alkaline reaction as sodium salts and can only be used in practice with x, 3-dimethylxanthine (theophylline) added.
Es wurde nun gefunden, daB man zu neutralen, therapeutisch wirksamen, schwefelhaltigen Quecksilberverbindunge n gelangt, wenn man Quecksilberverbindungen der allgemeinen Formel wobei R1 einen aromatischen oder hydroaromatischen Rest, der eine saure salzbildende Gruppe enthält, X eine -S OZ - N H-, - CO- N H- oder - N H - C O - N H-Gruppe und R2 eine Oxygruppe, die dusch Alkyl- oder Oxyalkylreste substituiert sein kann, bedeutet, in Form ihrer Salze mit Verbindungen der Formel wobei Y Sauerstoff, Schwefel oder die Iminogruppe bedeutet, oder deren Salzen umsetzt.It has now been found that neutral, therapeutically active, sulfur-containing mercury compounds are obtained if one uses mercury compounds of the general formula where R1 is an aromatic or hydroaromatic radical containing an acidic salt-forming group, X is an -S OZ - N H-, - CO- N H- or - NH - CO - N H group and R2 is an oxy group which is alkyl- or oxyalkyl radicals can be substituted in the form of their salts with compounds of the formula where Y denotes oxygen, sulfur or the imino group, or converts their salts.
Als Ausgangsstoffe kommen als Quecksilberverbindungen beispielsweise in Frage: N- (y-Oxymercuri-ß- oxypropoxy-propyl) -m-sulfonamidobenzoesäure, N - (y- Oxymercuri -ß-dioxypropoxy-propyl)-m-sulfonamidobenzoesäure, i-(ß-Carboxy-propionylamino)-phenyl-4-sulfonsäure-(y-oxymercuri.-ß-oxyäthoxy-propyl)-amid, i-(ß-Carboxy-propionylamino)-phenyl-4-sulfonsäure-(y-oxymercuri-ß-oxypropoxy-propyl)-amid, i-(ß-Carboxy-propionylamino)-phenyl-4-sulfonsäure-[y - oxymercuri - ß - (2 ', 3'- di.oxy-propoxy) -propyl]-amid, i-(ß-Carboxy-propionylamino)-phenyl-4-sulfonsäure-[y-oxYmercuri ß-(3'-oxy-butoxy)-propyl]-amid, N-(4-Carboxy-phenyl)-N'-(y-oxymercuri ß-methoxypropyl)-harnstoff, N-(4-Carboxy-phenyl)-N'-(y-oxymercuri ß-oxyäthoxypropyl)-harnstoff, N-(4-Carboxy-phenyl) -N'- (y - oxymercuii-ß - oxypropoxy-propyl)-harnstoff, N-(4-Carboxy-phenyl)-N'-[y-oxymercuri-ß-(2, 3-dioxypropoy-y)-propyl]-harnstoff, (N-y-Oxymercuri ß-oxy-propyl)-campheramidsäure, [N-y -Oxymercuri-ß- (oxyäthoxy) -propyl] - campheramidsäure, [N-y-Oxymercuri-ß- (oxypropoxy) -propyl]-campheramidsäure.For example, mercury compounds are used as starting materials in question: N- (y-Oxymercuri-ß- oxypropoxy-propyl) -m-sulfonamidobenzoic acid, N - (y-Oxymercuri -ß-dioxypropoxy-propyl) -m-sulfonamidobenzoic acid, i- (ß-Carboxy-propionylamino) -phenyl-4-sulfonic acid- (y-oxymercuri.-ß-oxyethoxy-propyl) -amide, i- (ß-Carboxy-propionylamino) -phenyl-4-sulfonic acid- (y-oxymercuri-ß-oxypropoxy-propyl) -amide, i- (ß-Carboxy-propionylamino) -phenyl-4-sulfonic acid- [y - oxymercuri - ß - (2 ', 3'- di.oxy-propoxy) -propyl] -amide, i- (β-carboxy-propionylamino) -phenyl-4-sulfonic acid- [γ-oxYmercuri ß- (3'-oxy-butoxy) -propyl] -amide, N- (4-carboxy-phenyl) -N '- (y-oxymercuri ß-methoxypropyl) -urea, N- (4-carboxy-phenyl) -N '- (y-oxymercuri ß-oxyethoxypropyl) urea, N- (4-carboxy-phenyl) -N'- (y - oxymercuri-ß - oxypropoxy-propyl) urea, N- (4-carboxy-phenyl) -N '- [y-oxymercuri-ß- (2, 3-dioxypropoy-y) -propyl] -urea, (N-y-oxymercuri ß-oxy-propyl) -campheramic acid, [N-y-oxymercuri-ß- (oxyethoxy) -propyl] campheramic acid, [N-y-oxymercuri-ß- (oxypropoxy) propyl] campheramic acid.
Als Umsetzungskomponente kommen z. B. in Frage 2-Mercapto-benzoxazol-carbonsäure-(6), 2-Mercaptobenzimidazöl-carbonsäure-(6), 2-Mercapto-benzthiazol-carbonsäure-(6) oder deren Salze.As an implementation component come z. B. in question 2-mercapto-benzoxazole-carboxylic acid- (6), 2-mercaptobenzimidazole-carboxylic acid- (6), 2-mercapto-benzthiazole-carboxylic acid- (6) or their salts.
Zweckmäßig führt man die Reaktion so aus, daß man zu Lösungen der Alkalisalze von Quecksilberverbindunzen der allzemeinen Formel 2-mercapto-benzoxazol-6-carbonsaures Natrium oder 2-mercapto-benzimidazol-6-carbonsaures Natriumoder 2-mercapto-benzthiazol-6-carbonsaures Natrium hinzufügt.The reaction is expediently carried out in such a way that solutions of the alkali salts of mercury compounds of the general formula are obtained 2-mercapto-benzoxazole-6-carboxylic acid sodium or 2-mercapto-benzimidazole-6-carboxylic acid sodium or 2-mercapto-benzothiazole-6-carboxylic acid sodium.
Aus den Lösungen lassen sich dann in einfacher Weise schwefelhaltige Quecksilberverbindungen der allgemeinen Formel in Form der Natriumsalze isolieren, wobei R1, X, Y und R2 die obengenannte Bedeutung haben.Sulfur-containing mercury compounds of the general formula can then be easily prepared from the solutions isolate in the form of the sodium salts, where R1, X, Y and R2 are as defined above.
Die neuen Verbindungen stellen wertvolle Diuretica däx, die sich in Wasser mit neutraler Reaktion lösen und die daher ohne Zusatz von i, 3-Dimethylxanthin (Theophyllin) verwendet werden können.The new compounds represent valuable diuretics that are found in Dissolve water with a neutral reaction and therefore without the addition of i, 3-dimethylxanthine (Theophylline) can be used.
Beispiel i Man versetzt eine Aufschlämmung von 7,8 Gewichtsteilen 2-Mercapto-benzoxazol-6-carbonsäure in 2o Volumteilen 2-n-Natronlauge mit einer Lösung von 22,4 Gewichtsteilen i-[N-(y-Oxymercuri-ß-methoxypropyl)-carbonamido]-2-phenoxy-.essigsaurem Natrium in 40 Volumteilen Wasser. Nachdem alles gelöst ist, filtriert man die Lösung durch eine Schicht A-Kohle und dampft das Filtrat im Hochvakuum ein. Man erhält 17,2 Teile des Di-Na-Salzes des i-[o-Carboxy-methoxy-(2')-benzamido]-2-methOxy-3-[6"-carboxy-benzoxazolyl- (2 ") -mercapto-mercuri] -propans, das 3 Mol Kristallwasser enthält.Example i A slurry of 7.8 parts by weight is added 2-mercapto-benzoxazole-6-carboxylic acid in 2o parts by volume of 2N sodium hydroxide solution with a Solution of 22.4 parts by weight of i- [N- (γ-oxymercuri-ß-methoxypropyl) carbonamido] -2-phenoxy-acetic acid Sodium in 40 parts by volume of water. After everything has dissolved, the solution is filtered through a layer of activated charcoal and evaporate the filtrate in a high vacuum. You get 17.2 parts of the di-Na salt of i- [o-carboxy-methoxy- (2 ') - benzamido] -2-methoxy-3- [6 "-carboxy-benzoxazolyl- (2 ") -mercapto-mercuri] -propane, which contains 3 moles of water of crystallization.
Beispiel 2 22 Gewichtsteile N-(4-Carboxyphenyl)-N'-allylharnstoff in 2ooo Gewichtsteilen Methanol werden mit 31 Gewichtsteilen Quecksilberacetat in iooo Volumteilen Methanol 4 Stunden am Rückfluß erhitzt. Die farblosen Kristalle werden abgesaugt, in 5o Volumteilen 2 n-Natronlauge gelöst und die Lösung filtriert. Das Filtrat wird zu 6o. Volumteilen 2 n-Schwefelsäure gegeben, der entstandene Niederschlag abgesaugt und gut mit Wasser gewaschen. Nach dem Trocknen erhält man _29 Gewichtsteile N-(4=Carboxyphenyl)-N'-(y-oxymercuri-ß-methoxy-propyl)-harnstoff.Example 2 22 parts by weight of N- (4-carboxyphenyl) -N'-allylurea in 2ooo parts by weight of methanol with 31 parts by weight of mercury acetate in 100 parts by volume of methanol heated under reflux for 4 hours. The colorless crystals are suctioned off, dissolved in 50 parts by volume of 2N sodium hydroxide solution and the solution is filtered. The filtrate becomes 6o. Given parts by volume of 2N sulfuric acid, the resulting precipitate Aspirated and washed well with water. After drying, 29 parts by weight are obtained N- (4 = carboxyphenyl) -N '- (γ-oxymercuri-ß-methoxy-propyl) -urea.
4,7. Gewichtsteile des N-(4-Carboxy-phenyl)-N'- (y-oxymercuri ß-methoxy-propyl)-harnstoffs in 2o Volumteilen n=Natronlauge werden mit 2,2 Gewichtsteilen 2-Mercapto-benzoxazol-6-carbonsäure versetzt. Die Lösung ergibt nach dem Filtrieren lind Eindampfen im Hochvakuum 6,.1 Gewichtsteile des Dinatriumsalzes des i-(p-Carboxyphenylureido)-2-methoxy-3-[6'-carboxybenzoxazolyl-(2')-mercaptomercuri] -propans, das 3 Mol Kristallwasser enthält.4.7. Parts by weight of the N- (4-carboxy-phenyl) -N'- (γ-oxymercuri ß-methoxy-propyl) -urea 2o parts by volume of n = sodium hydroxide solution are mixed with 2.2 parts by weight of 2-mercapto-benzoxazole-6-carboxylic acid offset. The solution gives after filtration and evaporation in a high vacuum 6, .1 Parts by weight of the disodium salt of i- (p-carboxyphenylureido) -2-methoxy-3- [6'-carboxybenzoxazolyl- (2 ') - mercaptomercuri] propane, which contains 3 moles of water of crystallization.
Beispiel 3 15,6 Gewichtsteile i-ß-Carboxypropionylaminophenyl-4-sulfonsäure-allylamid, das z. B. aus Sulfanilsäure-allylamid durch Erhitzen mit Bernsteinsäureanhydrid erhalten .werden kann, werden in 2ooo Gewichtsteilen Wasser heiß gelöst, mit einer Lösung von 20,4 Gewichtsteilen a-Acetoxy-mercuri-ß-methoxyhydrozimtsäure-methylester in iooo Gewichtsteilen Wasser versetzt und 5 Stunden auf dem Dampfbad erhitzt. Dann wird die heiße Lösung abdekantiert und der Rückstand mit Wasser gewaschen. Man löst die erhaltene Verbindung in 25 Volumteilen 2 n-Natronlauge, filtriert und gibt die Lösung in eine Mischung von 4 Volumteilen Eisessig und 5oo Volumteilen Wasser. Man erhält nachdem Absaugen und Trocknen im Exsikkator 18,8 Gewichtsteile i-ß-Carboxypropionylaminophenyl - 4- sulfonsäure - N' - [(y - oxymercuriß-oxy)-propyl]-amid.Example 3 15.6 parts by weight of i-ß-carboxypropionylaminophenyl-4-sulfonic acid allylamide, the Z. B. from sulfanilic acid allylamide by heating with succinic anhydride can be obtained, are dissolved in 2ooo parts by weight of hot water, with a Solution of 20.4 parts by weight of a-acetoxy-mercuri-ß-methoxyhydrocinnamic acid methyl ester added in 1,000 parts by weight of water and heated on the steam bath for 5 hours. then the hot solution is decanted off and the residue is washed with water. One solves the compound obtained in 25 parts by volume of 2N sodium hydroxide solution, filtered and gives the Solution in a mixture of 4 parts by volume of glacial acetic acid and 500 parts by volume of water. Man obtained after suctioning off and drying in a desiccator 18.8 parts by weight of i-ß-carboxypropionylaminophenyl - 4-sulfonic acid - N '- [(y - oxymercuriß-oxy) propyl] amide.
21,9 Gewichtsteile i-ß-Carboxypropionylamino-phenyl - 4 - sulfonsäure-N- (y-oxymercuri-ß-oxy-propyl)-amid werden in 8o Volumteilen n-Natronlauge gelöst und 8,8 Gewichtsteile 2-Mercapto-benzoxazol-6-carbonsäure zugefügt. Nach dem Filtrieren und Eindampfen im Hochvakuum erhält man 30,7 Gewichtsteile desDinatriümsalzes des i-(p-ß-Carboxy-propionylamido-benzol-sulfonsäure-amido)-3-[6'-carboxy-benzoxazolyl-(2')-mercapto-mercuri]-propanols-(2), das 2 Mol Kristallwasser enthält.21.9 parts by weight of i-ß-carboxypropionylamino-phenyl-4-sulfonic acid-N- (y-oxymercuri-ß-oxy-propyl) -amide are dissolved in 80 parts by volume of n-sodium hydroxide solution and 8.8 parts by weight of 2-mercapto-benzoxazole 6-carboxylic acid added. After filtration and evaporation in a high vacuum, 30.7 parts by weight of the dinatrium salt of i- (p-ß-carboxy-propionylamido-benzene-sulfonic acid-amido) -3- [6'-carboxy-benzoxazolyl- (2 ') - mercapto- mercuri] -propanols- (2), which contains 2 moles of water of crystallization.
Beispiel 4 13,6 Gewichtsteile i-ß-Carboxypropionylaminophenyl-4-sulfonsäureallyl-amid werden mit i5 Gewichtsteilen Quecksilberacetat in ioo Volumteilen Äthylenglykol q. Stunden auf dem Dampfbad erhitzt. Nach dem Filtrieren wird die Lösung in 5oo Gewichtsteile Wasser gegossen. Nach dem Stehen über Nacht wird das Wasser durch Dekantieren von der sirupartigen Masse abgetrennt und diese nochmals mit 5oo Gewichtsteilen Wasser digeriert. Nach dem Dekantieren wird die sirupartige Masse in 25 VOlumteilen 2n-Natronlauge in der Wärme gelöst, filtriert und in eine Mischung aus q. Volumteilen Eisessig und 500 Volumteilen Wasser getropft. Der Niederschlag wird abgesaugt, gut mit Wasser gewaschen und im Exsikkator getrocknet. Man erhält 18,5. Gewichtsteile i -ß - Carboxypropionylamino -phenyl-q.-sulfOnsäure-N - [y -oxymercuri-ß- oxyäthoxy-propyl] - amid.Example 4 13.6 parts by weight of i-ß-carboxypropionylaminophenyl-4-sulfonic acid allyl amide are mixed with 15 parts by weight of mercury acetate in 100 parts by volume of ethylene glycol q. Heated for hours on the steam bath. After filtering, the solution is poured into 500 parts by weight of water. After standing overnight, the water is separated from the syrupy mass by decanting and this is digested again with 500 parts by weight of water. After decanting, the syrupy mass is dissolved in 25 volumetric parts of 2N sodium hydroxide solution in the heat, filtered and poured into a mixture of q. Parts by volume of glacial acetic acid and 500 parts by volume of water were added dropwise. The precipitate is filtered off with suction, washed well with water and dried in a desiccator. 18.5 is obtained. Parts by weight of β-carboxypropionylamino-phenyl-q.-sulfonic acid-N - [γ-oxymercuri-β-oxyethoxy-propyl] amide.
5,9 Gewichtsteile i-ß-Carboxy-propionylaminophenyl - q. - sulfonsäure - (y - oxymercuri - ß - oxyäthoxypropyl)-amid werden in 2o Volumteilen n-Natronlauge gelöst; man setzt 1,95 Gewichtsteile 2-Mercaptobenzoxazol-6-carbonsäure zu, filtriert und dampft die Lösung im Hochvakuum ein. Man erhält 7,8 Gewichtsteile des Dinatriumsalzes des i-(p-ß-Carboxypropionylamido-benzol-sulfon-amido)-2-ß-oxy-äthOxy-3-[6'-carboxy-benzoxazolyl-(2')-mercapto-mercuri]-propäns, das mit 2 @Tol Wasser kristallisiert. Beispiel 5 25,8 Gewichtsteile N-[y-Oxymercuri-ß-oxypropoxypropyl]-m-sulfon-aznido-benzoesäureanhydrid, hergestellt nach dem Verfahren des Patents 923788, werden unter Eiskühlung zu 9,75 Gewichtsteilen 2-Mercapto-benzoxazol-6-carbonsäure in 5o VQlumteilen 2n-Natronlauge gegeben. Es entsteht eine klare Lösung, die nach dem Filtrieren im Hochvakuum eingedampft wird.5.9 parts by weight of i-ß-carboxy-propionylaminophenyl - q. - sulfonic acid - (y - oxymercuri - ß - oxyäthoxypropyl) -amid are n-caustic soda in 20 parts by volume solved; 1.95 parts by weight of 2-mercaptobenzoxazole-6-carboxylic acid are added, and the mixture is filtered and evaporate the solution in a high vacuum. 7.8 parts by weight of the disodium salt are obtained des i- (p-ß-carboxypropionylamido-benzene-sulfone-amido) -2-ß-oxy-ethoxy-3- [6'-carboxy-benzoxazolyl- (2 ') -mercapto-mercuri] -propane, which crystallizes with 2 @ tol water. Example 5 25.8 parts by weight of N- [γ-oxymercuri-β-oxypropoxypropyl] -m-sulfone-aznido-benzoic anhydride, prepared by the method of patent 923788, becomes 9.75 with ice cooling Parts by weight of 2-mercapto-benzoxazole-6-carboxylic acid in 50 parts by volume of 2N sodium hydroxide solution given. A clear solution is formed which, after filtering, evaporates in a high vacuum will.
Man erhält 36 Gewichtsteile des Dinatriumsalzes des i-(p-Carboxy-benzol-sulfon-amido)-2-ß-propoxy-3- [6'-carboxy-benzoxazolyl- (2') -mercapto-mercuri]-propans, das 3 Mol Kristallwasser enthält.36 parts by weight of the disodium salt of i- (p-carboxy-benzene-sulfone-amido) -2-ß-propoxy-3- [6'-carboxy-benzoxazolyl- (2 ') -mercapto-mercuri] -propane, the 3 moles of water of crystallization contains.
Beispiel 6 21,9 Gewichtsteile i-ß-Carboxy-propionylaminophenyl-q.-sulfonsäure-N'-(y-oxymercuri-ß-oxy-propyl)-amid, dessen Herstellung im Beispie13 beschrieben ist, werden in 40 Volumteilen 2n-Natronlauge in der Kälte gelöst und 7,76 Gewichtsteile 2-Mercaptobenzimidazol-6-carbonsäure zugegeben. Nach dem Filtrieren dampft man die Lösung im Hochvakuum ein.Example 6 21.9 parts by weight of i-ß-carboxy-propionylaminophenyl-q.-sulfonic acid-N '- (y-oxymercuri-ß-oxy-propyl) -amide, the production of which is described in Beispie13, 40 parts by volume of 2N sodium hydroxide solution Dissolved in the cold and 7.76 parts by weight of 2-mercaptobenzimidazole-6-carboxylic acid admitted. After filtering, the solution is evaporated in a high vacuum.
Man erhält 26,4 Gewichtsteile des Dinatriumsalzes des i-(p-ß-Carboxypropionyl-amido-benzol-sulfonamido) -3 - [6'-carboxy-benzimidazolyl- (2') -mercaptomercuri]-propanols-(2), das mit 3M01 Wasser kristallisiert.26.4 parts by weight of the disodium salt of i- (p-ß-carboxypropionyl-amido-benzene-sulfonamido) are obtained -3 - [6'-carboxy-benzimidazolyl- (2 ') -mercaptomercuri] -propanols- (2), the with 3M01 Water crystallizes.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF8648A DE940896C (en) | 1952-03-22 | 1952-03-22 | Process for the production of sulfur-containing mercury compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF8648A DE940896C (en) | 1952-03-22 | 1952-03-22 | Process for the production of sulfur-containing mercury compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE940896C true DE940896C (en) | 1956-03-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF8648A Expired DE940896C (en) | 1952-03-22 | 1952-03-22 | Process for the production of sulfur-containing mercury compounds |
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| Country | Link |
|---|---|
| DE (1) | DE940896C (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT99678B (en) * | 1921-09-21 | 1925-04-10 | Hoechst Ag | Process for the preparation of medicinally active mercury compounds. |
| DE550620C (en) * | 1927-01-25 | 1932-05-19 | Chinoin Gyogyszer Es Vegyeszet | Process for the preparation of therapeutically valuable organic mercury compounds |
| DE641285C (en) * | 1934-01-06 | 1937-01-26 | Chem Ind Basel | Process for the preparation of water-soluble heterocyclic mercury compounds |
-
1952
- 1952-03-22 DE DEF8648A patent/DE940896C/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT99678B (en) * | 1921-09-21 | 1925-04-10 | Hoechst Ag | Process for the preparation of medicinally active mercury compounds. |
| DE550620C (en) * | 1927-01-25 | 1932-05-19 | Chinoin Gyogyszer Es Vegyeszet | Process for the preparation of therapeutically valuable organic mercury compounds |
| DE641285C (en) * | 1934-01-06 | 1937-01-26 | Chem Ind Basel | Process for the preparation of water-soluble heterocyclic mercury compounds |
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