CH310729A - Process for the production of a new Schiff base. - Google Patents
Process for the production of a new Schiff base.Info
- Publication number
- CH310729A CH310729A CH310729DA CH310729A CH 310729 A CH310729 A CH 310729A CH 310729D A CH310729D A CH 310729DA CH 310729 A CH310729 A CH 310729A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- pyrimidine
- dimethyl
- schiff base
- aminomethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000002262 Schiff base Substances 0.000 title 1
- 150000004753 Schiff bases Chemical class 0.000 title 1
- DEOWHUDUQMOMEQ-UHFFFAOYSA-N 5-(aminomethyl)-2,6-dimethylpyrimidin-4-amine Chemical compound CC1=NC(C)=C(CN)C(N)=N1 DEOWHUDUQMOMEQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- OTANUNWCNKJPBC-UHFFFAOYSA-N 1-ethyl-3-(4-formylphenyl)urea Chemical compound CCNC(=O)NC1=CC=C(C=O)C=C1 OTANUNWCNKJPBC-UHFFFAOYSA-N 0.000 description 3
- -1 p-ethylureido-phenyl Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer neuen Schiffsehen Base. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer neuen Sehiffsehen Base, welches dadurch gekenn- zeiehnet ist, dass man auf 2,6-Dimethyl-4- i amino -5-aminomethyl-pyrimidin eine das Ra- dikal der Formel
EMI0001.0012
liefernde Verbindung einwirken lässt.
Als das Radikal der obigen Formel liefernde Verbin dungen seien genannt: p-Äthylureido-benz- aldehvd, p - Äthylureido - benzaldeliy dacetalc oder p-Äthylureido-benzaldehy ddiaeylderivate.
Das so erhaltene 5-(p-Ätliylureidobenzal- aminomethyl)-2,6-dimethyl-4-amino-py rimidin, das wahrscheinlich wenigstens in Lösung im Gleiehgewicht mit der Ringform 2,6-Diniethyl 2'-(p-äthylureido-phenyl)-1',2',3',4'-tetrahydro- pyrimido-(5',6' : 5,4) -pyrimidin steht, schmilzt bei 168-169 . Das Verfahrensprodukt soll als Chemotherapeuticum und als Zwischenpro dukt Verwendung finden.
<I>Beispiel:</I> Zu einer Lösung von 10 g Natrium in 400 em"- abs. Methanol werden 49 g 2,6-Di- niet.liyl-4-amino- 5 - aminomethyl - p7 r imidin-di- hy drochlorid gegeben, das Ganze kurz zum Sieden erhitzt, gekühlt und mit einer Lösung von 42 g p-Äthylureido-benzaldehyd in 250 cm3 abs. Methanol vermischt.
Man kocht 15 Minu ten, destilliert den Methanol im Vakuum ab, versetzt den Rückstand mit 200 cm3 Dioxan und kühlt unter Schütteln auf 0 . Das aus gefallene Produkt wird abgesaugt und aus Wasser umkristallisiert. Man erhält so 33 g, das sind 460/ & der Theorie, der bei 168-169 schmelzenden p-Äthylureido-benzalverbindung des 2,6-Dimethyl-4-amino-5-aminomethyl-pyr- imidins.
Method of manufacturing a new marine base. The subject of the present patent is a process for the production of a new Sehiffsehen base, which is characterized in that one has the radical of the formula on 2,6-dimethyl-4-amino -5-aminomethyl-pyrimidine
EMI0001.0012
supplying compound can act.
The following compounds which provide the radical of the above formula may be mentioned: p-ethylureido-benzaldehyde, p-ethylureido-benzaldeliy dacetalc or p-ethylureido-benzaldehyde diaeyl derivatives.
The 5- (p-Ätliylureidobenzal- aminomethyl) -2,6-dimethyl-4-aminopyrimidine, which is probably at least in solution in equilibrium with the ring form 2,6-diniethyl 2 '- (p-ethylureido-phenyl ) -1 ', 2', 3 ', 4'-tetrahydropyrimido- (5', 6 ': 5.4) -pyrimidine, melts at 168-169. The process product is intended to be used as a chemotherapeutic agent and as an intermediate product.
<I> Example: </I> 49 g of 2,6-di-niet.liyl-4-amino-5-aminomethyl-p7 r imidine-di are added to a solution of 10 g of sodium in 400 em "- abs. Methanol - given hydrochloride, the whole thing briefly heated to the boil, cooled and mixed with a solution of 42 g of p-ethylureido-benzaldehyde in 250 cm3 of absolute methanol.
It is boiled for 15 minutes, the methanol is distilled off in vacuo, the residue is mixed with 200 cm3 of dioxane and cooled to 0 while shaking. The precipitated product is filtered off with suction and recrystallized from water. This gives 33 g, that is 460% of theory, of the p-ethylureido-benzal compound of 2,6-dimethyl-4-amino-5-aminomethyl-pyrimidine which melts at 168-169.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH310729T | 1952-06-27 | ||
| CH309034T | 1955-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH310729A true CH310729A (en) | 1955-10-31 |
Family
ID=25735563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH310729D CH310729A (en) | 1952-06-27 | 1952-06-27 | Process for the production of a new Schiff base. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH310729A (en) |
-
1952
- 1952-06-27 CH CH310729D patent/CH310729A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1230031B (en) | Process for the preparation of derivatives of naphthalene-1, 4, 5, 8-tetracarboxylic acid diimide | |
| CH310729A (en) | Process for the production of a new Schiff base. | |
| CH310724A (en) | Process for the production of a new Schiff base. | |
| CH310722A (en) | Process for the production of a new Schiff base. | |
| CH310721A (en) | Process for the production of a new Schiff base. | |
| CH310726A (en) | Process for the production of a new Schiff base. | |
| CH310727A (en) | Process for the production of a new Schiff base. | |
| CH310730A (en) | Process for the production of a new Schiff base. | |
| DE843412C (en) | Process for the preparation of 2- (3,4-dioxy-phenyl) -morpholine | |
| CH544835A (en) | Benzofuran optical brighteners | |
| CH310725A (en) | Process for the production of a new Schiff base. | |
| CH310728A (en) | Process for the production of a new Schiff base. | |
| AT293393B (en) | Process for the preparation of benzodiazepin-2-ones or salts thereof | |
| AT236404B (en) | Process for the preparation of new benzenesulfonyl-alkylene-semicarbazides | |
| DE1038047B (en) | Process for the preparation of N-aminoalkylated iminodibenzyls and their salts | |
| CH361573A (en) | Process for the preparation of new 5-aminomethyl-pyrimidines | |
| DE729849C (en) | Process for the preparation of ketones from heterocyclic compounds | |
| AT48347B (en) | Process for the preparation of azidyl compounds of alkylated iminopyrimidines. | |
| AT296316B (en) | Process for the preparation of new benzodiazepine derivatives and their N-4-oxides | |
| AT277277B (en) | PROCESS FOR MANUFACTURING NEW SULFONYL URENE DERIVATIVES | |
| AT231461B (en) | Process for the preparation of new benzenesulfonyl semicarbazides | |
| AT236937B (en) | Process for the production of new basic substituted anthradipyrazoles | |
| AT71170B (en) | Process for the preparation of azidyl derivatives of the xanthine series. | |
| AT217023B (en) | Process for the preparation of dialkylaminoalkyl ethers of aromatic alcohols | |
| AT233582B (en) | Process for the preparation of new iminodibenzyl derivatives |