CH146259A - Process for the production of a new urea derivative. - Google Patents
Process for the production of a new urea derivative.Info
- Publication number
- CH146259A CH146259A CH146259DA CH146259A CH 146259 A CH146259 A CH 146259A CH 146259D A CH146259D A CH 146259DA CH 146259 A CH146259 A CH 146259A
- Authority
- CH
- Switzerland
- Prior art keywords
- urea derivative
- production
- new
- new urea
- phosgene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000003672 ureas Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 150000002605 large molecules Chemical class 0.000 claims description 2
- 229920002521 macromolecule Polymers 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 claims 1
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- LJDZFAPLPVPTBD-UHFFFAOYSA-N nitroformic acid Chemical class OC(=O)[N+]([O-])=O LJDZFAPLPVPTBD-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines neuen Harnstoffderivates. Es wurde gefunden, dass technisch wert volle Körper der Konstitution
EMI0001.0003
wobei R und RI Reste von Verbindungen der Benzol- oder Naphthalinreihe bedeuten, entstehen, wenn man Diarylharnstoffdiearbon- säuren mit Aminophenolen,
welche keine Sulfo- oder freie Carboxylgruppe enthalten und bei denen wenigstens eine o- oder p-Stellung zur Hydroxylgruppe unbesetzt ist, bei Gegenwart von wasserentziehenden Mitteln, wie Phos- phortrichlorid kondensiert, oder wem)
man die Kondensationsprodukte aus Aminocarbon- säuren oder deren entsprechenden Halogen- substitutionsprodukten mit Aminophenolen der angegebenen Konstitution, also Amino- arylaminophenole, die sich auch durch Konden sation von Nitrocarbonsäuren mit Amino- phenülen und nachfolgender Reduktion er halten lassen, mit Phosgen behandelt.
Vorliegendes Patent bezieht sich nun auf ein Verfahren zur Darstellung eines neuen Harnstoffderivates, dadurch gekennzeichnet, dass man m-Aminobenzoesätire durch Be handlung mit Phosgen in die Diphenylharii- stoff-m-m'-diearbonsäure überführt Lind diese mit m-Aminopheno! in Gegenwarteineswasser- entziehenden Mittels kondensiert.
Der neue Körper ist ein violettgraues Pulver, er ist in den üblichen organischen Lösungsmitteln unlöslich und schmilzt in rohem Zustande bei<B>255-257'</B> unter Zer setzung. Er ist trotz der Abwesenheit von Sulfo- und Carboxylgruppen in dem grossen Molekül in Form der Alkalisalze in Wasser für technische Verwendung genügend löslich und besitzt eine gewisse Affinität zur pflanz lichen Faser, welche es ermöglicht, Baum wollwaren mit den Lösungen zu imprägnieren.
<I>Beispiel:</I> 274 Teile m-Aminobeiizoesäure und<B>272</B> Teile Natriumacetat werden in<B>1000</B> Teilen Wasser gelöst und in die Lösung bei<B>60'</B> Phosgen bis zur Sättigung eingeleitet. Die aus der Lösung sich ausscheidende Diphenyl- harnstoff-m <B>.</B> m'-dieai,bonsätire wird nach dem .Abfiltrieren zunächst mit Salzsäure, danach mit Wasser gewaschen und getrocknet und besitzt dann den Fp. <B>290-293 0.</B>
In ein Gemisch von<B>30</B> Teilen Diphenyl- harnstoff-in <B>.</B> ra'-diearbonsäure, 22 Teilen in- Aminophenol und<B>300</B> Teilen Dimethylauilin lässt man bei<B>70-80 0 10</B> Teile Phosphor- trichlorid eintropfen und erhitzt nach dem Eintragen noch<B>5</B> Stunden auf 1201. Die Re aktionsmasse wird dann in Salzsäure ge gossen, der entstandene Niederschlag abge saugt und mit Sodalösung bis zur Alkalität verrührt.
Nach Ablassen des Dimethylanilins wird das erhaltene Kondensationsprodukt gereinigt.
Process for the production of a new urea derivative. It has been found that technically valuable bodies of the constitution
EMI0001.0003
where R and RI mean residues of compounds of the benzene or naphthalene series, are formed when diarylurea diacids with aminophenols,
which contain no sulfo or free carboxyl group and in which at least one o- or p-position to the hydroxyl group is unoccupied, in the presence of dehydrating agents such as phosphorus trichloride condenses, or who)
the condensation products of aminocarboxylic acids or their corresponding halogen substitution products with aminophenols of the stated constitution, ie aminoarylaminophenols, which can also be obtained by condensation of nitrocarboxylic acids with aminophenulins and subsequent reduction, are treated with phosgene.
The present patent now relates to a process for the preparation of a new urea derivative, characterized in that m-aminobenzoesätire are converted into diphenylhariistoff-m-m'-diacid by treatment with phosgene, and this with m-aminopheno! condensed in the presence of a water-removing agent.
The new body is a violet-gray powder, it is insoluble in the usual organic solvents and melts in the raw state at <B> 255-257 '</B> with decomposition. Despite the absence of sulfo and carboxyl groups in the large molecule in the form of alkali salts, it is sufficiently soluble in water for technical use and has a certain affinity for vegetable fibers, which makes it possible to impregnate cotton goods with the solutions.
<I> Example: </I> 274 parts of m-aminobeiizoic acid and <B> 272 </B> parts of sodium acetate are dissolved in <B> 1000 </B> parts of water and added to the solution at <B> 60 '</ B> Phosgene introduced until saturation. The diphenylurea-m'-dieai, bonsätire which separates out of the solution is, after being filtered off, washed first with hydrochloric acid and then with water and dried and then has the melting point 290 -293 0. </B>
In a mixture of <B> 30 </B> parts of diphenylurea-in <B>. </B> ra'-diacid, 22 parts of in-aminophenol and <B> 300 </B> parts of dimethylauiline are added Drop in 70-80 0 10 parts of phosphorus trichloride and heat for a further <B> 5 </B> hours at 1201 after entry. The reaction mass is then poured into hydrochloric acid and the precipitate formed is suctioned off and mixed with soda solution until it is alkaline.
After the dimethylaniline has been drained off, the condensation product obtained is purified.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE146259X | 1928-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH146259A true CH146259A (en) | 1931-04-15 |
Family
ID=5671235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH146259D CH146259A (en) | 1928-11-02 | 1929-10-24 | Process for the production of a new urea derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH146259A (en) |
-
1929
- 1929-10-24 CH CH146259D patent/CH146259A/en unknown
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