DE824055C - Process for the preparation of almond acid hexamethylenetetramine - Google Patents
Process for the preparation of almond acid hexamethylenetetramineInfo
- Publication number
- DE824055C DE824055C DE1949P0043809 DEP0043809D DE824055C DE 824055 C DE824055 C DE 824055C DE 1949P0043809 DE1949P0043809 DE 1949P0043809 DE P0043809 D DEP0043809 D DE P0043809D DE 824055 C DE824055 C DE 824055C
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- hexamethylenetetramine
- almond acid
- almond
- acid hexamethylenetetramine
- 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
Links
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 title claims description 14
- 235000010299 hexamethylene tetramine Nutrition 0.000 title claims description 7
- 239000004312 hexamethylene tetramine Substances 0.000 title claims description 7
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 3
- 229960002510 mandelic acid Drugs 0.000 claims description 3
- 235000011437 Amygdalus communis Nutrition 0.000 claims 1
- 241000220304 Prunus dulcis Species 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 235000020224 almond Nutrition 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/18—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von mandelsaurem Hexamethylentetramin Das in den Arzneischatz als wertvolles Harndesinfiziens eingegangene mandelsaure Hexamethylentetra.min wird nach dem Verfahren der Patentschrift 672494 in der Weise hergestellt, daß man Hexamethylentetramin und Mandelsäure vorzugsweise in äquimolekularen Mengen in Gegenwart von Lösungsmitteln aufeinander einwirken läßt und aus der Lösung das Umsetzungsprodukt in kristalliner Form zur Abscheidung bringt. Es werden hierbei Ausbeuten von etwa 6o "/o erhalten.Process for the preparation of almond acid hexamethylenetetramine The Almond acid hexamethylene tetra, which has entered the medicinal treasure as a valuable urine disinfectant is prepared by the method of patent specification 672494 in such a way that Hexamethylenetetramine and mandelic acid preferably in equimolecular amounts in the presence allows solvents to act on one another and the reaction product from the solution brings to the deposition in crystalline form. There are yields of about 6o "/ o received.
Wie nun gefunden wurde, läßt sich die Ausbeute an mandelsaurem Hexamethylentetramin quantitativ gestalten, wenn man die beiden Komponenten in Abwesenheit von Lösungsmitteln aufeinander wirken läßt. Das erhaltene Umsetzungsprodukt zeigt die gleiche Wirksamkeit, wie das in bisheriger Weise dargestellte Präparat. Durch das erfindungsgemäße Verfahren wird eine erhebliche Verbilligung dieses wichtigen Arzneimittels erzielt, (1a, abgesehen von der Auslaeutesteigerung, das Lösungsmittel sowie Zeit und Kosten der Aufarbeitung eingespart werden.As has now been found, the yield of almond acid hexamethylenetetramine Make quantitative if you consider the two components in the absence of solvents can interact. The reaction product obtained shows the same effectiveness, like the preparation shown in the previous way. By the method according to the invention a considerable reduction in the price of this important drug is achieved, (1a, apart of the increase in maturity, the solvent, and the time and cost of processing can be saved.
Beispiel 32 Gewichtsteile Mandelsäure und 28 Gewichtsteile Hexamethylentetramin werden bei 1050 durch etwa '/2stündiges Verrühren zusammengeschmolzen. Man erhält zunächst eine glasige, farblose Masse, die nach einiger Zeit durchkristallisiert. Das Produkt ist wasserlöslich und hat die gleiche pharmakologische und therapeutische Wirksamkeit wie die bereits beschriebene Verbindung.EXAMPLE 32 parts by weight of mandelic acid and 28 parts by weight of hexamethylenetetramine are melted together at 1050 by stirring for about 1/2 hour. First of all, a glassy, colorless mass is obtained, which crystallizes through after some time. The product is soluble in water and has the same pharmacological and therapeutic effectiveness as the compound already described.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1949P0043809 DE824055C (en) | 1949-05-25 | 1949-05-25 | Process for the preparation of almond acid hexamethylenetetramine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1949P0043809 DE824055C (en) | 1949-05-25 | 1949-05-25 | Process for the preparation of almond acid hexamethylenetetramine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE824055C true DE824055C (en) | 1951-12-10 |
Family
ID=579091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1949P0043809 Expired DE824055C (en) | 1949-05-25 | 1949-05-25 | Process for the preparation of almond acid hexamethylenetetramine |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE824055C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE964052C (en) * | 1954-09-03 | 1957-05-16 | Badische Anilin & Soda Fabarik | Process for the production of bacteriostatically active and urestone-releasing hexamethylene tetramine complex salts |
| DE1056136B (en) * | 1956-12-21 | 1959-04-30 | Bayer Ag | Process for the preparation of a molecular compound from p-aminobenzenesulfonylthiourea (sulfathiourea) and hexamethylenetetramine |
| WO2017210122A1 (en) * | 2016-06-03 | 2017-12-07 | Albemarle Corporation | Processes for producing methenamine mandelate |
-
1949
- 1949-05-25 DE DE1949P0043809 patent/DE824055C/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE964052C (en) * | 1954-09-03 | 1957-05-16 | Badische Anilin & Soda Fabarik | Process for the production of bacteriostatically active and urestone-releasing hexamethylene tetramine complex salts |
| DE1056136B (en) * | 1956-12-21 | 1959-04-30 | Bayer Ag | Process for the preparation of a molecular compound from p-aminobenzenesulfonylthiourea (sulfathiourea) and hexamethylenetetramine |
| WO2017210122A1 (en) * | 2016-06-03 | 2017-12-07 | Albemarle Corporation | Processes for producing methenamine mandelate |
| US20190127388A1 (en) * | 2016-06-03 | 2019-05-02 | Albemarle Corporation | Processes for producing methenamine mandelate |
| JP2019518751A (en) * | 2016-06-03 | 2019-07-04 | アルベマール・コーポレーシヨン | Manufacturing process of methenamine mandelate |
| US10683303B2 (en) | 2016-06-03 | 2020-06-16 | Albemarle Corporation | Processes for producing methenamine mandelate |
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