CH169509A - Process for the preparation of a derivative of 5,5-phenylethylhydantoin. - Google Patents
Process for the preparation of a derivative of 5,5-phenylethylhydantoin.Info
- Publication number
- CH169509A CH169509A CH169509DA CH169509A CH 169509 A CH169509 A CH 169509A CH 169509D A CH169509D A CH 169509DA CH 169509 A CH169509 A CH 169509A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenylethylhydantoin
- soluble
- preparation
- methyl
- derivative
- Prior art date
Links
- WADHXSHSHULALT-UHFFFAOYSA-N 5-(2-phenylethyl)imidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1CCC1=CC=CC=C1 WADHXSHSHULALT-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- ATNGRRVWWJVDBA-UHFFFAOYSA-N 1-(1-cyano-3-phenylpropyl)-3-methylurea Chemical compound C1(=CC=CC=C1)CCC(C#N)NC(=O)NC ATNGRRVWWJVDBA-UHFFFAOYSA-N 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines Derivates des ö,5-Phenyläthylhydantoins. Es wurde gefunden, dass man 1-Alkyl- bezw. -Aralkyl-5,5-phenyläthylhydantoine da durch herstellen kann, dass man Verbindungen der allgemeinen Formel
EMI0001.0005
worin Ri eine gesättigte oder ungesättigte Alkyl- oder Aralkylgruppe, R2 einen Wasser stoff oder eine substituierte oder nicht sub stituierte Carboxylgruppe und R3 eine sub stituierte oder nicht substituierte Carboxyl- gruppe bedeuten,
mit geeigneten Konden sationsmitteln behandelt.
Die hier gewählte Bezeichnung "substi- tuierte Carboxylgruppell betrifft folgende Gruppen: -CON1I2, -CN, -CONHCI, -C00- Alkyl, -CONH-COOH, -COCI, -CSNH2.
Zwecks Herstellung der Hydantoine wer den die Verbindungen der oben angegebenen allgemeinen Formel mit Kondensationsmitteln, wie Säuren, Alkalien und Metallsalzen be- handelt oder gegebenenfalls nur in Gegen wart von Wasser auf höhere Temperaturen erhitzt.
Die vorliegende Erfindung betrifft ein Ver fahren zur Darstellung von 1-Methyl-5,5- pheriyläthylhydantoin, welches dadurch ge kennzeichnet ist, dass man Pheriyläthylmethyl- ureidoacetonitril mit Salzsäure behandelt.
<I>Beispiel:</I> 1 Gewichtsteil Phenyläthylmethylureido- acetonitril
EMI0001.0031
wird mit dem vierfachen Volumen 20 %iger Salzsäure übergossen, wobei unter Selbst erwärmung das Ureid in Lösung geht und das Hydantoin sich meist sofort auszuschei den beginnt. Zur Vervollständigung der Re aktion erhitzt man während einer Stunde auf dem Dampfbad. Nach dein Absaugen wird das Rohprodukt aus Alkohol umkristallisiert.
Man erhält das 1-Methyl-5,5-phenyläthyl- hydantoin in fast quantitativer Ausbeute in farblosen langen Nadeln vom Schmelzpunkt 202-2031. Es ist leicht löslich in heissem, schwer in kaltem Alkohol, leicht löslich in Eisessig, mässig löslich in Chloroform, schwer löslich in Äther; in Wasser fast unlöslich löst es sich bei Gegenwart von Alkalien und wird mit Säuren unverändert ausgefällt.
0,2994 gr verbrauchen nach gjeldahl 27,49 cm3 n10 H2S04 für C12111402N2, berechnet 12,84 % N gefunden 12,86 % N Das Produkt soll in der Therapie Ver wendung finden.
Process for the preparation of a derivative of ö, 5-phenylethylhydantoin. It has been found that 1-alkyl or. -Aralkyl-5,5-phenyläthylhydantoine can be produced by using compounds of the general formula
EMI0001.0005
where Ri is a saturated or unsaturated alkyl or aralkyl group, R2 is a hydrogen or a substituted or unsubstituted carboxyl group and R3 is a substituted or unsubstituted carboxyl group,
treated with suitable condensation agents.
The term "substituted carboxyl group" chosen here relates to the following groups: -CON1I2, -CN, -CONHCI, -C00-alkyl, -CONH-COOH, -COCI, -CSNH2.
For the purpose of preparing the hydantoins, the compounds of the general formula given above are treated with condensing agents such as acids, alkalis and metal salts or, if appropriate, only heated to higher temperatures in the presence of water.
The present invention relates to a process for the preparation of 1-methyl-5,5-pheriylethylhydantoin, which is characterized in that Pheriyläthylmethyl- ureidoacetonitrile is treated with hydrochloric acid.
<I> Example: </I> 1 part by weight of phenylethylmethylureidoacetonitrile
EMI0001.0031
four times the volume of 20% hydrochloric acid is poured over it, whereby the ureide dissolves under self-heating and the hydantoin usually begins to separate immediately. To complete the reaction, the mixture is heated on the steam bath for one hour. After you have filtered off with suction, the crude product is recrystallized from alcohol.
The 1-methyl-5,5-phenylethylhydantoin is obtained in almost quantitative yield in colorless long needles with a melting point of 202-2031. It is easily soluble in hot alcohol, poorly in cold alcohol, easily soluble in glacial acetic acid, moderately soluble in chloroform, hardly soluble in ether; Almost insoluble in water, it dissolves in the presence of alkalis and is precipitated unchanged with acids.
0.2994 gr use according to gjeldahl 27.49 cm3 n10 H2S04 for C12111402N2, calculated 12.84% N found 12.86% N The product should be used in therapy.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH169509T | 1934-06-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169509A true CH169509A (en) | 1934-05-31 |
Family
ID=4421610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169509D CH169509A (en) | 1934-06-06 | 1932-12-16 | Process for the preparation of a derivative of 5,5-phenylethylhydantoin. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169509A (en) |
-
1932
- 1932-12-16 CH CH169509D patent/CH169509A/en unknown
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