CH259662A - Process for the preparation of a biguanide derivative. - Google Patents
Process for the preparation of a biguanide derivative.Info
- Publication number
- CH259662A CH259662A CH259662DA CH259662A CH 259662 A CH259662 A CH 259662A CH 259662D A CH259662D A CH 259662DA CH 259662 A CH259662 A CH 259662A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- preparation
- diiodophenyl
- biguanide derivative
- isopropyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000004283 biguanides Chemical class 0.000 title description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 229940123208 Biguanide Drugs 0.000 claims description 3
- GHWMYAKHPIIZNH-UHFFFAOYSA-N 3,4-diiodoaniline Chemical compound NC1=CC=C(I)C(I)=C1 GHWMYAKHPIIZNH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 230000000078 anti-malarial effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 N'-3 Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SWHSXWLSBBYLGM-UHFFFAOYSA-N 2-[(2-carboxyphenoxy)methoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCOC1=CC=CC=C1C(O)=O SWHSXWLSBBYLGM-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
verfahren zur Herstellung eines Biguanidderivates. Die vorliegende Erfindung betrifft. ein Verfahren zur Herstellung von N'-3,4-Dijocl- phenyl-N'-methyl-N@'-isopropylbiguanid, wel ches ein wertvolles ehemotherapeutisehes 'Mit tel ist oder als Zwisehenprodukt für die Her stellung von ehemotherapeutisehen @4litteln verwendet werden kann. Es ist insbesondere ein wertvolles Antimalariamittel.
Erfindungsgemäss wird die besagte neue Verbindung-, nämlich N'-3,4-Dijodphenyl-hl'- methyl-N'-isopropylbiguanid, dadurch erbal- ten, class man N'-lllethyl-N'-isopropy ldicyan- diamid mit. 3,4-Dijodanilin umsetzt.
Die Umsetzung erfolgt zweckmässig durch Erhitzen eines Salzes des Amins mit dem sub stituierten Dicyancliamid in Gegenwart eines Lösungsmittels, z. B. Wasser oder ss-Ätho-xy- ät.hanol.
Das N'-3,4-Dijodphenyl-N'-methyl-l@@'-iso- propylbiguanid stellt eine starke Base dar, welche mit organischen und anorganischen Säuren beständige Salze ergibt, die in man chen Fällen in Wasser leicht löslich sind. Die Salze lassen sich dadurch herstellen, dass die Base in wässrigen Lösungen der Säure gelöst und hierauf das Wasser verdampft wird, doch können sie in trockener Form bequemer durch Vermischen der Komponenten in einem organischen Lösungsmittel, wie z. B. Aceton, oder in einem Alkohol, in welchem die Salze spärlich löslich sind, hergestellt werden.
Auf diese Weise kann man beispiels weise die Salze mit Essigsäure, Milehsäure, Methansulfonsäure, Methy lendisalicylsäure, llethylen-bis-ss-oiynaphthoesäure und Salz säure bequem herstellen.
Das folgende Beispiel diene zur Erläute rung der Erfindung. <I>Beispiel,:</I> Ein Gemisch von 14 Teilen N'-Methyl-N'- isopropyldicyandiamid und 38,2 Teilen 3,4- Dijodanilin-chlorhydrat in 125 Teilen ss-Äth- oxyäthanol wird während 3 Stunden unter Rückfluss zum Sieden erhitzt. Hierauf lässt man das Gemisch abkühlen, worauf abfiltriert wird. Der feste Rückstand wird mit kaltem Äthylalkohol gewaschen und aus Wasser um kristallisiert.
Auf diese Weise erhält man N'-3,4-Dijodphenyl-N'-methyl-N'-isopropyl- biguanid in Form seines Monohydrochlorids, welches bei 235 C schmilzt.
process for the production of a biguanide derivative. The present invention relates to. a process for the production of N'-3,4-Dijocl- phenyl-N'-methyl-N @ '- isopropylbiguanid, wel ches a valuable erstotherapeutisehes' means is or can be used as an intermediate product for the manufacture of erstotherapeutisehen @ 4littel . It is a particularly valuable antimalarial drug.
According to the invention, the said new compound, namely N'-3,4-diiodophenyl-hl'-methyl-N'-isopropylbiguanide, is obtained by adding N'-IIIethyl-N'-isopropyl dicyanodiamide. 3,4-Diiodaniline converts.
The reaction is conveniently carried out by heating a salt of the amine with the sub-substituted dicyancliamide in the presence of a solvent, e.g. B. water or ss-ethoxy-xy-ethanol.
The N'-3,4-diiodophenyl-N'-methyl-l @@ '- isopropyl biguanide is a strong base which, with organic and inorganic acids, results in stable salts which in some cases are easily soluble in water. The salts can be prepared in that the base is dissolved in aqueous solutions of the acid and then the water is evaporated, but they can be more conveniently in dry form by mixing the components in an organic solvent, such as. B. acetone, or in an alcohol in which the salts are sparingly soluble.
In this way, for example, the salts with acetic acid, lactic acid, methanesulfonic acid, methylene disalicylic acid, llethylene-bis-ss-olynaphthoic acid and hydrochloric acid can be conveniently prepared.
The following example serves to explain the invention. <I> Example: </I> A mixture of 14 parts of N'-methyl-N'-isopropyldicyandiamide and 38.2 parts of 3,4-diiodaniline chlorohydrate in 125 parts of β-ethoxyethanol is refluxed for 3 hours heated to boiling. The mixture is then allowed to cool and it is filtered off. The solid residue is washed with cold ethyl alcohol and crystallized from water.
In this way, N'-3,4-diiodophenyl-N'-methyl-N'-isopropyl biguanide is obtained in the form of its monohydrochloride, which melts at 235.degree.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB259662X | 1945-10-08 | ||
| GB170946X | 1946-09-17 | ||
| CH254800T | 1946-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH259662A true CH259662A (en) | 1949-01-31 |
Family
ID=27178018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH259662D CH259662A (en) | 1945-10-08 | 1946-10-08 | Process for the preparation of a biguanide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH259662A (en) |
-
1946
- 1946-10-08 CH CH259662D patent/CH259662A/en unknown
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