CH200904A - 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
- CH200904A CH200904A CH200904DA CH200904A CH 200904 A CH200904 A CH 200904A CH 200904D A CH200904D A CH 200904DA CH 200904 A CH200904 A CH 200904A
- Authority
- CH
- Switzerland
- Prior art keywords
- nitrogen
- containing aromatic
- aromatic aldehyde
- preparation
- chloroethyldiphenylamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- -1 nitrogen-containing aromatic aldehyde Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 2
- LCSRYMIEHTXEPZ-UHFFFAOYSA-N n-(2-chloroethyl)-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCl)C1=CC=CC=C1 LCSRYMIEHTXEPZ-UHFFFAOYSA-N 0.000 claims description 2
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 claims description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- DIDOBGBVBCPOEE-UHFFFAOYSA-N 4-(2-chloroethyl)aniline Chemical compound NC1=CC=C(CCCl)C=C1 DIDOBGBVBCPOEE-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 I3erstellung eines stick stoffhaltigen aromatischen Aldehyds.
Das Verfahren ist dadurch gekennzeiohnet, dass in-an N-Chloräthyldiphenylamin, N-Methyl- formanilid und Phosphoroxychlorid aufein- a.nder einwirken lä.sst. Der so erhältliche p-Chloräthy lphenylaminobenzald-ehyd stellt ein schwach gefärbtes @01 dar. Es soll zur Synthese von Farbstoffen u. a. dienen.
Beispiel: Man versetzt allmählich 53 Gewichtsteile N-Oxyäthyldiphenylamin mit 42 Gewichts teilen P'hosphoroxychlorid bei ca.<B>60',</B> er wärmt zwen Stunden auf 90 bis 1.00;' und tropft hierzu naoh Abkühlen bei etwa 20' eine Mischung von 68 Gewichtsteilen N- 3Tethylformanilid und 77 Gewichtsteilen Phosphoroxychlorid in 100 Gewichtsteilen Benzol zu.
Nach mehrstündigem Erwärmen auf 4.5 bis <B>50'</B> und Austragen auf Eis trennt man die benzolische.Schicht ab, wäscht mehr mals mit oalz@s!äurohaltigem Wasser und er- hält dann ,den p-Chloräthylphenylaminoben,z- aldeby d nach Abd@estillieren des Benzols als schwach gefärbtes Öl in sehr guter Aus beute.
Process for the preparation of a nitrogen-containing aromatic aldehyde. The subject of the present patent is a process for the production of a nitrogen-containing aromatic aldehyde.
The process is characterized in that in-an N-chloroethyldiphenylamine, N-methylformanilide and phosphorus oxychloride act on one another. The thus obtainable p-Chloräthy lphenylaminobenzald-ehyd is a weakly colored @ 01. It is said to be used for the synthesis of dyes u. a. serve.
Example: 53 parts by weight of N-oxyethyldiphenylamine are gradually added to 42 parts by weight of phosphorus oxychloride at about <B> 60 ', </B> it is heated to 90 to 1.00 for two hours;' and after cooling at about 20 ', add a mixture of 68 parts by weight of N-3-ethylformanilide and 77 parts by weight of phosphorus oxychloride in 100 parts by weight of benzene.
After several hours of warming to 4.5 to 50 'and discharging onto ice, the benzene layer is separated off, washed several times with water containing oaline and then obtained the p-chloroethylphenylamine above, e.g. aldeby d after distilling off the benzene as a weakly colored oil in very good yield.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200904X | 1935-04-12 | ||
| CH192574T | 1936-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200904A true CH200904A (en) | 1938-10-31 |
Family
ID=25722299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200904D CH200904A (en) | 1935-04-12 | 1936-04-02 | Process for the preparation of a nitrogen-containing aromatic aldehyde. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH200904A (en) |
-
1936
- 1936-04-02 CH CH200904D patent/CH200904A/en unknown
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