AT138386B - Process for the preparation of bismuth salts of mercured organic compounds. - Google Patents
Process for the preparation of bismuth salts of mercured organic compounds.Info
- Publication number
- AT138386B AT138386B AT138386DA AT138386B AT 138386 B AT138386 B AT 138386B AT 138386D A AT138386D A AT 138386DA AT 138386 B AT138386 B AT 138386B
- Authority
- AT
- Austria
- Prior art keywords
- bismuth salts
- acid
- preparation
- organic compounds
- mercured
- Prior art date
Links
- 150000001621 bismuth Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 4
- 150000002894 organic compounds Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000002731 mercury compounds Chemical class 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- -1 mercury thiobenzimidazole carboxylic acid Chemical compound 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 3
- 150000002730 mercury Chemical class 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- MFEVGQHCNVXMER-UHFFFAOYSA-L 1,3,2$l^{2}-dioxaplumbetan-4-one Chemical compound [Pb+2].[O-]C([O-])=O MFEVGQHCNVXMER-UHFFFAOYSA-L 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000003 Lead carbonate Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Description
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Verfahren zur Darstellung von Wismutsalzen mercurierter organischer Verbindungen.
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Beispiel 2 : 60 Natriumsalz der 4-[(ss-Oxyquecksilber-γ-methoxyallyl)-oxy]-3-acetaminobenzol- arsinsäure- (l), gelost in 180 cm3 Wasser, werden mit einer Lösung von 48'5 g Wismutnitrat versetzt und das entstandene Wismutsalz, das folgende Zusammensetzung aufweist, in der im Beispiel 1 angegebenen Weise rein gewonnen :
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Die 4-Allyloxy-3-acetaminobenzolarsinsäure-(1) erhält man durch Umsetzung von 4-0xy-3-aeetamino- benzolarsinsäure- (1) mit Allylbromid in alkalischer Lösung. Die so dargestellte Säure ist gut löslich in Methylalkohol und kristallisiert aus Wasser in weissen Nädelchen.
Die Mercurierung erfolgt nach dem in der Patentschrift Nr. 99678 beschriebenen Verfahren.
Beispiel 3 : 39-5 y Natriumsalz der Quecksilberthiobenzimidazolarsinsäure-(5) [hergestellt durch Einwirkung eines anorganischen Quecksilbersalzes auf die Thiobenzimidazolarsinsäure- (5) ] werden in der zehnfachen Menge Wasser gelöst. Dann fügt man unter kräftigem Rühren eine Lösung von 48-5 g Wismutnitrat in 48#5 g Glycerin und 97 cm3 Wasser hinzu. Hiebei scheidet sich das basische Wismutsalz der Arsinsäure als farbloser Niederschlag aus, der abgesaugt, mit Wasser gewaschen und im Vakuum getrocknet wird.
Das Salz entspricht wahrscheinlich folgender Formel :
EMI2.1
Als Ausgangsprodukt dient die 3. 4-Diaminobenzolarsinsäure- (1), die durch Umsetzung mit Ealiumxanthogenat und durch Behandeln mit frisch gefälltem Bleicarbonat in die Thiobenzimidazolarsinsäure-(5) übergeführt wird.
Beispiel 4 : Durch Umsetzung von 31'5 g Natriumsalz der Quecksilberthiobenzimidazolcarbon- säure- (5), gelöst in 3'15l Wasser, mit einer Lösung von 48-5 5 g Wismutnitrat wie in Beispiel 3 erhält man das farblose Wismutsalz analoger Zusammensetzung. Die Quecksilberthiobenzimidazolcarbonsäure-(5) wird durch Einwirkung eines anorganischen Quecksilbersalzes auf die Thiobenzimidazolcarbonsäure-(5) (Patentschrift Nr. 102313) erhalten.
Beispiel 5 : Zu einer Lösung von 34#9 g Natriumsalz der Quecksilberthiobenzimidazolsulfon-
EMI2.2
gesättigter, wässeriger Kochsalzlösung zulaufen. Dann wird mit 65 cm3 10% iger Natronlauge bis zur Lackmusneutralität abgestumpft und das entstandene farblose Wismutsalz abgesaugt, mit Wasser gewaschen und im Vakuum getrocknet.
Als Ausgangsprodukt dient die3. 4-DiaminobenzoIsulfonsäure- (l), die durch Umsetzung mit Natrium xanthogenat das Na-Salz der Thiobenzimidazolsulfonsäure- (5) liefert, das aus verdünntem Alkohol in schönen, farblosen Blättchen kristallisiert. Durch Umsetzung des letzteren mit einem anorganischen Quecksilbersalz in wässeriger Lösung entsteht die Quecksilberthiobenzimidazolsulfonsäure-(5).
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<Desc / Clms Page number 1>
Process for the preparation of bismuth salts of mercured organic compounds.
EMI1.1
EMI1.2
Example 2: A solution of 48.5 g of bismuth nitrate is added to 60 sodium salt of 4 - [(β-oxymercury-γ-methoxyallyl) -oxy] -3-acetaminobenzolarsinic acid- (I), dissolved in 180 cm3 of water and the resulting bismuth salt, which has the following composition, obtained pure in the manner indicated in Example 1:
EMI1.3
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The 4-allyloxy-3-acetaminobenzolaric acid- (1) is obtained by reacting 4-0xy-3-aeetaminobenzolaric acid- (1) with allyl bromide in an alkaline solution. The acid represented in this way is readily soluble in methyl alcohol and crystallizes from water in white needles.
The mercuration is carried out according to the method described in Patent Specification No. 99678.
Example 3: 39-5 y sodium salt of mercury thiobenzimidazolaric acid (5) [prepared by the action of an inorganic mercury salt on thiobenzimidazolaric acid (5)] are dissolved in ten times the amount of water. A solution of 48-5 g of bismuth nitrate in 48 # 5 g of glycerol and 97 cm3 of water is then added with vigorous stirring. The basic bismuth salt of arsic acid separates out as a colorless precipitate, which is filtered off with suction, washed with water and dried in vacuo.
The salt probably corresponds to the following formula:
EMI2.1
The starting product is 3,4-diaminobenzolarsin acid (1), which is converted into thiobenzimidazolarsin acid (5) by reaction with potassium xanthate and treatment with freshly precipitated lead carbonate.
Example 4: By reacting 31.5 g of the sodium salt of mercury thiobenzimidazole carboxylic acid (5), dissolved in 3.15 l of water, with a solution of 48-5.5 g of bismuth nitrate as in Example 3, the colorless bismuth salt of analogous composition is obtained. The thiobenzimidazole mercury carboxylic acid (5) is obtained by the action of an inorganic mercury salt on the thiobenzimidazole carboxylic acid (5) (Patent No. 102313).
Example 5: To a solution of 34 # 9 g of the sodium salt of mercury thiobenzimidazole sulfone
EMI2.2
run in saturated, aqueous saline solution. Then it is blunted with 65 cm3 of 10% sodium hydroxide solution to litmus neutrality and the resulting colorless bismuth salt is suctioned off, washed with water and dried in vacuo.
The 3 is used as the starting product. 4-DiaminobenzoIsulfonsäure- (l), which by reaction with sodium xanthogenat provides the Na salt of thiobenzimidazolesulfonsäure- (5), which crystallizes from diluted alcohol in beautiful, colorless flakes. The reaction of the latter with an inorganic mercury salt in an aqueous solution produces the mercury thiobenzimidazole sulfonic acid (5).
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Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE138386X | 1928-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT138386B true AT138386B (en) | 1934-07-25 |
Family
ID=5667297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT138386D AT138386B (en) | 1928-12-03 | 1929-10-14 | Process for the preparation of bismuth salts of mercured organic compounds. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT138386B (en) |
-
1929
- 1929-10-14 AT AT138386D patent/AT138386B/en active
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