CH200907A - Process for the preparation of a nitrogen-containing aromatic aldehyde. - Google Patents
Process for the preparation of a nitrogen-containing aromatic aldehyde.Info
- Publication number
- CH200907A CH200907A CH200907DA CH200907A CH 200907 A CH200907 A CH 200907A CH 200907D A CH200907D A CH 200907DA CH 200907 A CH200907 A CH 200907A
- Authority
- CH
- Switzerland
- Prior art keywords
- nitrogen
- containing aromatic
- aromatic aldehyde
- preparation
- aldehyde
- Prior art date
Links
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- -1 nitrogen-containing aromatic aldehyde Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 claims description 3
- FOAQOAXQMISINY-UHFFFAOYSA-N 4-morpholin-4-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1N1CCOCC1 FOAQOAXQMISINY-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- WBMGILSHAZPPNW-UHFFFAOYSA-N 6-amino-1,4-bis(2-chloroethyl)cyclohexa-2,4-diene-1-carbaldehyde Chemical compound ClCCC1(C=O)C(C=C(C=C1)CCCl)N WBMGILSHAZPPNW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- DNRDOYZBRNVGGF-UHFFFAOYSA-N n-(2,2-dichloroethyl)aniline Chemical compound ClC(Cl)CNC1=CC=CC=C1 DNRDOYZBRNVGGF-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines stickstoffhaltigen aromatischen Aldehyds. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines stick- stoffhaltigen aromatischen Aldehyds. Das Verfahren ist dadurch .gekennzeichnet, dass:
man N-Di-chloräthyl-anilin, N-Methylform- anilid und Phosphoroxychlorid aufeinander einwirken lässt und .in dem so erhaltenen p-Di-(chlorälhyl)-amino-benzaldehyd durch Behandlung mit einem verseifenden Mittel das Chlor gegen eine Sauerstoffbrücke aus tauscht. Der so erhältliche p-Morpholino- benzaIdehyd kristallisiert in feinen farb losen Kristallen: vom F.
P. 6ss bis<B>67'.</B> Er soll zur Synthese, von Farbstoffen u. a. die nen.
<I>Beispiel:</I> Zu 169 Gewichtsteilen Phosphoroxychlorid gibt man bei<B>N</B> allmählich 91 Gewichts teile N-Di-oxyäthyl=anilin und -erwärmt das Gemisch noch.
,einige Zeit auf 90 bis 10,0.'. Nach dem Abkühlen lässt man bei 10 bis <B>15'</B> allmählich ein Gemisch von 135 Gewichts- teilen N-Methylformanilid und 154 Gewichts- teilen Phosphoroxychlorid zutropfen, er wärmt noch einige Stunden auf 45 bis<B>50'</B> und trägt auf Eis aus.
Der entstandene p-Di-(chloräthyl)-aminobenzaldehyd scheidet sich als schwach :gefärbtes Öl ab, welches nach kurzem Rühren zu feinen, praktisch reinen Kristallen erstarrt.
Der Aldehyd kristallisiert aus Alkohol in :derben langen Prismen vom Schmelzpunkt<B>88,5'.</B> Dieser wird mit etwa ,der 15fachen Menge 50%igem Alkohol und 1,05 Mol :Soda unter Rühren am Rückflusskühler gekocht. mach Abdastil- lieren des Alkohole erhält man den p-Mor- pholinabenzal,dehyd als :
schwach gefärbtes, in der Kälte zu Kristallen erstarrendes <B>01.</B> Durch Umkristallisieren aus sehr wenig Alkohol erhält man :den Ald-e & yd in feinen farblosen Kristallen vom Schmelzpunkt 66 bis 67 . Er ist ausserordentlich löslich in organischen Mitteln wie Alkohol, Essigester, Aceton, Äther usw.
Process for the preparation of a nitrogen-containing aromatic aldehyde. The present patent relates to a process for the production of a nitrogen-containing aromatic aldehyde. The procedure is characterized in that:
N-dichloroethyl aniline, N-methylform anilide and phosphorus oxychloride are allowed to act on one another and the chlorine in the p-di (chloroethyl) amino benzaldehyde thus obtained is exchanged for an oxygen bridge by treatment with a saponifying agent. The p-morpholinobenzaldehyde that can be obtained in this way crystallizes in fine, colorless crystals: from F.
P. 6ss to <B> 67 '. </B> It should be used for synthesis, dyes and the like. a. serve.
<I> Example: </I> 91 parts by weight of N-dioxyethyl = aniline are gradually added to 169 parts by weight of phosphorus oxychloride at <B> N </B> and the mixture is warmed up.
'For some time to 90 to 10.0.'. After cooling, a mixture of 135 parts by weight of N-methylformanilide and 154 parts by weight of phosphorus oxychloride is gradually added dropwise at 10 to 15 '; it is heated to 45 to 50' for a few hours / B> and carries out on ice.
The resulting p-di- (chloroethyl) -aminobenzaldehyde separates out as a weakly colored oil, which solidifies to fine, practically pure crystals after brief stirring.
The aldehyde crystallizes from alcohol in: coarse long prisms with a melting point of <B> 88.5 '. </B> This is boiled with about 15 times the amount of 50% alcohol and 1.05 mol: soda while stirring on the reflux condenser. When the alcohol is removed, the p-morpholinabenzal is obtained, dehydrogenated as:
weakly colored <B> 01. </B> which solidifies into crystals in the cold. Recrystallization from very little alcohol gives: Ald-e & yd in fine colorless crystals with a melting point of 66 to 67. It is extremely soluble in organic agents such as alcohol, ethyl acetate, acetone, ether, etc.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200907X | 1935-04-12 | ||
| CH192574T | 1936-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200907A true CH200907A (en) | 1938-10-31 |
Family
ID=25722302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200907D CH200907A (en) | 1935-04-12 | 1936-04-02 | Process for the preparation of a nitrogen-containing aromatic aldehyde. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH200907A (en) |
-
1936
- 1936-04-02 CH CH200907D patent/CH200907A/en unknown
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