DE539179C - Process for the preparation of heterocyclic bases of the aminoimidazoline series - Google Patents
Process for the preparation of heterocyclic bases of the aminoimidazoline seriesInfo
- Publication number
- DE539179C DE539179C DEI34226D DEI0034226D DE539179C DE 539179 C DE539179 C DE 539179C DE I34226 D DEI34226 D DE I34226D DE I0034226 D DEI0034226 D DE I0034226D DE 539179 C DE539179 C DE 539179C
- Authority
- DE
- Germany
- Prior art keywords
- aminoimidazoline
- weight
- parts
- series
- preparation
- 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
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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Darstellung von heterocyclischen Basen der Aminoimidazolin-Reihe Es wurde gefunden, daß man leicht und in guter Ausbeute Basen der Aminoimidazolinreihe erhält, wenn man die Äther von Äthylenthioharnstoffen mit oder ohne Ver dünnungs- Die erhaltenen Basen sind in organischen Lösungsmitteln mit Ausnahme von Äther sehr leicht löslich. Sie lösen sich in Wasser mit stark alkalischer Reaktion. Die Basen sollen als Zwischenprodukte für die Darstellung von Farbstoffen und Färbereihilfsprodukten Verwendung finden.Process for the preparation of heterocyclic bases of the aminoimidazoline series It has been found that bases of the aminoimidazoline series are obtained easily and in good yield if the ethers of ethylene thioureas are diluted with or without Ver The bases obtained are very easily soluble in organic solvents with the exception of ether. They dissolve in water with a strongly alkaline reaction. The bases are intended to be used as intermediates for the preparation of dyes and auxiliary products for dyeing.
Beispiele r. 5o Gewichtsteile Äthylenthioharnstoffjodmethvlat (aus Äthvlenthioharnstoff und lTethyljodid, Kristalle aus Alkohol. F. i37°) und 4.4 Gewichtsteile p-Toluidin werden in 25o Gewichtsteilen Amylalkohol gekocht, bis die Mercaptanentwicklung beendet ist, dann mit Wasserdampf destilliert und aus der filtrierten Lauge mit Alkalien des Tolylaminoimidazolin gefällt. Von anhaftendem Toluidin kann es durch Waschen mit Äther befreit werden. Es kristallisiert aus Wasser in langen Nadeln vom Schmelzpunkt 133 bis mittel mit primären oder sekundären, aromatischen oder hydroaromatischen Aminen umsetzt. Die Umsetzung verläuft nach folgender allgemeiner Gleichung: r34°. Das entsprechende Phenylaminoimidazolin (weiße Blättchen aus Wasser kristallisiert) schmilzt bei r22°.Examples r. 50 parts by weight of ethylene thiourea iodine methoxide (from Ethylene thiourea and ethyl iodide, crystals of alcohol. F. i37 °) and 4.4 parts by weight p-Toluidine is boiled in 250 parts by weight of amyl alcohol until the evolution of mercaptan is finished, then distilled with steam and extracted from the filtered liquor with Alkalis of tolylaminoimidazoline precipitated. Adhesive toluidine can get through Wash with ether to be freed. It crystallizes from water in long needles from melting point 133 to medium with primary or secondary, aromatic or converts hydroaromatic amines. The implementation is more general as follows Equation: r34 °. The corresponding phenylaminoimidazoline (white flakes made from water crystallized) melts at r22 °.
2. zoo Gewichtsteile Äthylenthioharnstoff werden mit 125 Gewichtsteilen Dimethylsulfat in 25o Gewichtsteilen Alkohol unter Kühlung verrührt, bis alles gelöst ist, der Alkohol abgedampft und der Rückstand mit 5oo Gewichtsteilen p-Toluidin auf 13o° erhitzt und verrührt, bis die Mercaptanentwicklung beendet ist. Die weitere Aufarbeitung geschieht wie in Beispiel z.2. zoo parts by weight of ethylene thiourea are mixed with 125 parts by weight Stir dimethyl sulfate in 250 parts by weight of alcohol with cooling until everything is dissolved is, the alcohol evaporated and the residue with 500 parts by weight of p-toluidine heated to 130 ° and stirred until the evolution of mercaptan has ended. The other Work-up happens as in example z.
Auf analoge Weise kann man Äthy lenthioharnstoffäther mit anderen Aminen, z. B. Cyclohexvlanilin, Naphthvlamin usw., umsetzen. Es sind ebenfalls weiße kristallisierte Basen, die sich in organischen Lösungsmitteln leicht lösen und mit Pikrinsäure schwer lösliche Salze bilden.Ethyl thiourea ether can be used in an analogous manner with others Amines, e.g. B. Cyclohexvlanilin, Naphthvlamin, etc., implement. They are also white crystallized bases that easily dissolve in organic solvents and with Picric acid forms poorly soluble salts.
3. Verwendet man an Stelle von p-Toluidin Cyclohexylamin und verfährt im übrigen, wie in Beispiel 1 angegeben, so erhält man das Cyclohexylaminoimidazolin vom F. io2° (aus Chlorbenzol kristallisiert).3. Use cyclohexylamine instead of p-toluidine and proceed otherwise how given in Example 1, the cyclohexylaminoimidazoline is obtained from the F. io2 ° (crystallized from chlorobenzene).
4. 5o Gewichtsteile Äthylenthioharnstoffjodmethylat, entsprechend dem im Beispiel i beschriebenen Produkt, und 44 Gewichtsteile Monomethylanilin werden in 25o Gewichtsteilen Ainylalkohol gekocht bis zur Beendigung der Mercaptanentwicklung und dann in gleicher Weise weiterbehandelt, wie in Beispiel 1 beschrieben ist. Das erhaltene N-(Plienylmethyl-) aminoimidazolin schmilzt nach dem Umkristallisieren aus Wasser bei 131'. Es bildet ein schwer lösliches Pikrat.4. 50 parts by weight of ethylene thiourea iodomethylate, accordingly the product described in Example i, and 44 parts by weight of monomethylaniline Boiled in 250 parts by weight of ainyl alcohol until the evolution of mercaptan has ended and then treated further in the same way as described in Example 1. That The N- (plienylmethyl-) aminoimidazoline obtained melts after recrystallization from water at 131 '. It forms a sparingly soluble picrate.
5. An Stelle von 12o Gewichtsteilen Dimethylsulfat wird die äquivalente Menge Diäthylsulfat, wie im Beispiel 2 beschrieben, mit Zoo Gewichtsteilen Äthylenthioharnstoff in 25o Gewichtsteilen Alkohol unter Kühlung so lange verrührt, bis vollständige Lösung eingetreten ist. Nach dem Verdampfen des Alkohols wird der Rückstand mit 5oo Gewichtsteilen p-Toluidin versetzt und auf etwa i3o° erhitzt, bis die Mercaptanentwicklung beendet ist. Die weitere Aufarbeitung erfolgt, wie im Beispiel 1 beschrieben.5. Instead of 120 parts by weight of dimethyl sulfate, the equivalent Amount of diethyl sulfate, as described in Example 2, with zoo parts by weight of ethylene thiourea Stirred in 250 parts by weight of alcohol with cooling until complete Solution has occurred. After evaporation of the alcohol, the residue becomes with 500 parts by weight of p-toluidine are added and the mixture is heated to about 130 ° until the evolution of mercaptan is finished. The further work-up is carried out as described in Example 1.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI34226D DE539179C (en) | 1928-04-28 | 1928-04-28 | Process for the preparation of heterocyclic bases of the aminoimidazoline series |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI34226D DE539179C (en) | 1928-04-28 | 1928-04-28 | Process for the preparation of heterocyclic bases of the aminoimidazoline series |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE539179C true DE539179C (en) | 1931-11-23 |
Family
ID=7188655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI34226D Expired DE539179C (en) | 1928-04-28 | 1928-04-28 | Process for the preparation of heterocyclic bases of the aminoimidazoline series |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE539179C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1030349B (en) * | 1955-12-19 | 1958-05-22 | Wander Ag Dr A | Process for the preparation of 2- (3, 4-dioxy-phenyl-amino) -imidazoline |
| US2938038A (en) * | 1960-05-24 | X-dihydroxyphenylamino | ||
| US20100331384A1 (en) * | 2007-12-21 | 2010-12-30 | Universidad Del Pais Vasco/Euskal Herriko Unibertsitatea | Guanidine based compounds |
-
1928
- 1928-04-28 DE DEI34226D patent/DE539179C/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2938038A (en) * | 1960-05-24 | X-dihydroxyphenylamino | ||
| DE1030349B (en) * | 1955-12-19 | 1958-05-22 | Wander Ag Dr A | Process for the preparation of 2- (3, 4-dioxy-phenyl-amino) -imidazoline |
| US20100331384A1 (en) * | 2007-12-21 | 2010-12-30 | Universidad Del Pais Vasco/Euskal Herriko Unibertsitatea | Guanidine based compounds |
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