CH169939A - Process for the preparation of 1-amino-4-bromoanthraquinone-2-sulfonic acid chloride. - Google Patents
Process for the preparation of 1-amino-4-bromoanthraquinone-2-sulfonic acid chloride.Info
- Publication number
- CH169939A CH169939A CH169939DA CH169939A CH 169939 A CH169939 A CH 169939A CH 169939D A CH169939D A CH 169939DA CH 169939 A CH169939 A CH 169939A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- sulfonic acid
- preparation
- bromoanthraquinone
- acid chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- QHVDMXMRCQFJNU-UHFFFAOYSA-N 1-amino-4-bromo-9,10-dioxoanthracene-2-sulfonyl chloride Chemical compound C1=CC=C2C(=O)C3=C(Br)C=C(S(Cl)(=O)=O)C(N)=C3C(=O)C2=C1 QHVDMXMRCQFJNU-UHFFFAOYSA-N 0.000 title claims description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- -1 1-amino-4-bromoanthraquinone-2-sulfonic acid phosphorus pentachloride Chemical compound 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung des 1-Amino-4-bromanthraehinon-2-sulfosäurechlorids. Gegenstand dieses Patentes ist ein Ver fahren zur Darstellung des 1-Amino-4-brom- anthrachinon- 2 -sulfosäurechlorids, welches darin besteht, dass man auf das Natriumsalz der 1-Amino-4-bromanthrachinon-2-sulfosäure Phosphorpentachlorid zweckmässig in Gegen wart von Phosphoroxycblorid einwirken lässt.
Die so erhaltene Verbindung hat einen Schmelzpunkt von etwa 209-2101, sie lässt sich aus Chlorbenzol umkristallisieren und ist gegen Wasser ziemlich beständig. Die neue Verbindung kann als Zwischenprodukt für die Herstellung von Farbstoffen Verwen dung finden.
<I>Beispiel:</I> Zu 1200 Gewichtsteilen Phosphoroxy- chlorid, 108 Gewichtsteilen Phosphorpenta- chlorid und 90 Gewichtsteilen Kochsalz wer den 171 Gewichtsteile 1-Amino-4-broman- thrachinon-2-sulfosäure gegeben. Man erwärmt etwa 8 Stunden auf dem Dampfbade auf 90-95 , gibt dann 300 Gewichtsteile Chlor benzol zu und rührt noch 1-2 Stunden bei etwa 90-950. Die Reaktionsmasse wird heiss abgesaugt und der Rückstand mit 300 Gewichtsteilen Chlorbenzol ausgezogen.
Die Filtrate werden zusammen im Vakuum ein gedampft und ergeben in guter Ausbeute das rohe Sulfochlorid. Löst man dasselbe in heissem Benzol, filtriert und dampft das Lö sungsmittel im Vakuum ab, so erhält man das Sulfochlorid leicht in wohl ausgebildeten Kristallblättchen von rotoranger Farbe. Es schmilzt bei etwa<B>207'.</B> Aus Chlorbenzol lässt es sich umkristallisieren und schmilzt dann bei 209-210'. Gegen Wasser ist das reine Chlorid recht beständig. Mit Aminen erhält man leicht die Sulfamide, mit Anilin, z.
B. das Anilid vom Schmelzpunkt 220 , mit Oxäthylamin das Oxäthylamid vom Schmelzpunkt 206-207', beide in wohlaus gebildeten Kristallen.
Process for the preparation of 1-amino-4-bromanthraehinone-2-sulfonic acid chloride. The subject of this patent is a process for the preparation of the 1-amino-4-bromo-anthraquinone-2-sulfonic acid chloride, which consists in the fact that the sodium salt of 1-amino-4-bromoanthraquinone-2-sulfonic acid phosphorus pentachloride is expediently present lets act of phosphorus oxycloid.
The compound thus obtained has a melting point of about 209-2101, it can be recrystallized from chlorobenzene and is fairly resistant to water. The new compound can be used as an intermediate in the manufacture of dyes.
<I> Example: </I> 171 parts by weight of 1-amino-4-bromanthrachinone-2-sulfonic acid are added to 1200 parts by weight of phosphorus oxychloride, 108 parts by weight of phosphorus pentachloride and 90 parts by weight of sodium chloride. The mixture is heated to 90-95 for about 8 hours on the steam bath, then 300 parts by weight of chlorobenzene are added and the mixture is stirred for a further 1-2 hours at about 90-950. The reaction mass is filtered off with suction while hot and the residue is extracted with 300 parts by weight of chlorobenzene.
The filtrates are evaporated together in vacuo and give the crude sulfochloride in good yield. If the same is dissolved in hot benzene, filtered and the solvent evaporated in vacuo, the sulfochloride is easily obtained in well-formed crystal flakes of red-orange color. It melts at around <B> 207 '. </B> It can be recrystallized from chlorobenzene and then melts at 209-210'. The pure chloride is quite resistant to water. The sulfamides are easily obtained with amines, with aniline, e.g.
B. the anilide with a melting point of 220, with oxethylamine the oxethylamide with a melting point of 206-207 ', both in well-formed crystals.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE169939X | 1932-02-22 | ||
| CH165827T | 1933-02-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH169939A true CH169939A (en) | 1934-06-15 |
Family
ID=25718161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH169939D CH169939A (en) | 1932-02-22 | 1933-02-17 | Process for the preparation of 1-amino-4-bromoanthraquinone-2-sulfonic acid chloride. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH169939A (en) |
-
1933
- 1933-02-17 CH CH169939D patent/CH169939A/en unknown
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