CH178405A - Process for the preparation of 4-amino-3-ethoxy-2'-chloro-diphenylamine. - Google Patents
Process for the preparation of 4-amino-3-ethoxy-2'-chloro-diphenylamine.Info
- Publication number
- CH178405A CH178405A CH178405DA CH178405A CH 178405 A CH178405 A CH 178405A CH 178405D A CH178405D A CH 178405DA CH 178405 A CH178405 A CH 178405A
- Authority
- CH
- Switzerland
- Prior art keywords
- diphenylamine
- chloro
- ethoxy
- amino
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000975 dye Substances 0.000 claims description 5
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
- UEUIKXVPXLWUDU-UHFFFAOYSA-N 4-diazoniobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000000987 azo dye Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 2
- 229940008406 diethyl sulfate Drugs 0.000 claims description 2
- 239000012021 ethylating agents Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 229950000244 sulfanilic acid Drugs 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- XRYSCSFJNUNNAU-UHFFFAOYSA-N n-chloro-n-phenylaniline Chemical compound C=1C=CC=CC=1N(Cl)C1=CC=CC=C1 XRYSCSFJNUNNAU-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung des 4-Amino-3-äthoxy-2'-chlor-diphenylamins. Gegenstand des vorliegenden Zusatzpa tentes ist ein Verfahren zur Darstellung des 4-Amino-3-äthoxy-2'-chlor-diphenylamins,wel- ches dadurch gekennzeichnet ist, dass man das Dinatriumsalz des durch saure Kupplung von diazotierter Sulfanilsäure mit 3-Oxy-2'- ohlor-diphenylamin erhaltenen Azofarbstoffes mit einem äthylierenden Mittel behandelt und sodann den so erhaltenen,
an der Oxy- gruppe äthylierten Farbstoff durch Spaltung der Azobindung mittelst eines reduzierenden Mittels in das freie 4-Amino-3-äthoxy-2'- chlor-diphenylamin überführt.
Die so erhaltene neue Verbindung soll als Zwischenprodukt für die Herstellung von Farbstoffen Verwendung finden.
<I>Beispiel:</I> 67,2 Gewichtsteile des Dinatriumsalzes des durch saure Kupplung von diazotierter Sulfanilsäure mit 3-Oxy-2'-chlordiphenylamin erhaltenen Farbstoffes werden iii 400 Volum- teilen Wasser gelöst und auf<B>500</B> C erwärmt. Alsdann werden bei 50 bis<B>550</B> C innerhalb 15 Minuten 32,5 Volumteile Diäthylsulfat eingetropft und eine halbe Stunde bei 85 bis 90 o C nachgerührt.
Die so erhaltene Lö sung des an der Oxygruppe äthylierten Farb stoffes wird zur Spaltung mit-200 Volum- teilen 42 o/oiger Natriumsulfhydratlösunig ver setzt und 3 Stunden bei 75 bis 8011 C ge rührt, wobei sich unter Entfärbung das 4 Amino-3-äthoxy-2'-chlor-diphenylamin als schwach rötlich gefärbte, kristalline Masse abscheidet zur Reinigung wird das auf üb- licfie Weise isolierte Rohprodukt aus ver dünnter Salzsäure unikristallisiert,
wobei das salzsaure Salz in Form von farblosen, feinen Nädelchen erhalten wird. Das freie Amin kristallisiert aus Ligroin in langen, seidig glänzenden, zu Büscheln verwachsenen Nadeln vom Schmelzpunkt 82 bis 83 C (unkorrigiert). Das gleiche 4-Amirio-3-äthoxy-2'-chlor- diphenylamin erhält man auch, wenn man das obengenannte Dinatriumsalz in alkoho lischer Lösung mit Äthylbromid kocht und das Alkylierungsprodukt nach einer der üb lichen Reduktionsmethoden spaltet.
Process for the preparation of 4-amino-3-ethoxy-2'-chloro-diphenylamine. The subject of the present additional patent is a process for the preparation of 4-amino-3-ethoxy-2'-chloro-diphenylamine, which is characterized in that the disodium salt of sulfanilic acid diazotized by acid coupling with 3-oxy-2 '- treated azo dye obtained by chloro-diphenylamine with an ethylating agent and then the thus obtained,
Dye ethylated on the oxy group is converted into the free 4-amino-3-ethoxy-2'-chloro-diphenylamine by cleavage of the azo bond by means of a reducing agent.
The new compound obtained in this way is said to be used as an intermediate for the preparation of dyes.
<I> Example: </I> 67.2 parts by weight of the disodium salt of the dye obtained by acidic coupling of diazotized sulfanilic acid with 3-oxy-2'-chlorodiphenylamine are dissolved in 400 parts by volume of water and adjusted to <B> 500 </ B > C warms. Then 32.5 parts by volume of diethyl sulfate are added dropwise at 50 to 550 C within 15 minutes and the mixture is subsequently stirred at 85 to 90 ° C for half an hour.
The resulting solution of the dye ethylated on the oxy group is cleaved with -200 parts by volume of 42% sodium sulfhydrate solution and stirred for 3 hours at 75 to 8011 ° C., the 4-amino-3-ethoxy being discolored -2'-chloro-diphenylamine separates as a slightly reddish colored, crystalline mass. For cleaning, the crude product isolated in the usual way is unicrystallized from dilute hydrochloric acid,
the hydrochloric acid salt being obtained in the form of colorless, fine needles. The free amine crystallizes from ligroin in long, silky, shiny needles with a melting point of 82 to 83 C (uncorrected) that have grown together into tufts. The same 4-Amirio-3-ethoxy-2'-chlorodiphenylamine is also obtained when the above disodium salt is boiled in an alcoholic solution with ethyl bromide and the alkylation product is cleaved by one of the usual reduction methods.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE178405X | 1932-08-31 | ||
| CH176029T | 1933-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH178405A true CH178405A (en) | 1935-07-15 |
Family
ID=25719780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH178405D CH178405A (en) | 1932-08-31 | 1933-07-29 | Process for the preparation of 4-amino-3-ethoxy-2'-chloro-diphenylamine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH178405A (en) |
-
1933
- 1933-07-29 CH CH178405D patent/CH178405A/en unknown
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