CH189028A - Process for the preparation of 2-amino-1,3-di- (methylsulfonyl) -benzene. - Google Patents
Process for the preparation of 2-amino-1,3-di- (methylsulfonyl) -benzene.Info
- Publication number
- CH189028A CH189028A CH189028DA CH189028A CH 189028 A CH189028 A CH 189028A CH 189028D A CH189028D A CH 189028DA CH 189028 A CH189028 A CH 189028A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzene
- amino
- methylsulfonyl
- preparation
- azo dye
- Prior art date
Links
- JDIRRCVAVBWXIY-UHFFFAOYSA-N 2,6-bis(methylsulfonyl)aniline Chemical compound CS(=O)(=O)C1=CC=CC(S(C)(=O)=O)=C1N JDIRRCVAVBWXIY-UHFFFAOYSA-N 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000987 azo dye Substances 0.000 claims description 5
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 4
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- XNEFVTBPCXGIRX-UHFFFAOYSA-N methanesulfinic acid Chemical compound CS(O)=O XNEFVTBPCXGIRX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- -1 alkali metal salt Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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 Herstellung von 2-Amino-1,3-di-(methylsnlfonyl)-benzol. Gegenstand des vorliegenden Zusatzpa tentes ist ein Verfahren zur Herstellung von 2-Amino-1,3-di-(methylsulfonyl)-benzol, wel ches dadurch gekennzeichnet ist, dass man ein Alkalisalz des durch Kupplung von di- azotiertem 2,
6-Dichloranilin mit o-gresol er hältlichen Azofarbstoffes bei erhöhter Tempe ratur und unter Druck mit einem Alkalisalz der Methansulfinsäure umsetzt und den so erhaltenen Azofarbstoff durch Einwirken eines Reduktionsmittels aufspaltet.
Die erhaltene Verbindung stellt einen wertvollen Ausgangsstoff, beispielsweise für die Herstellung von Farbstoffen dar.
Beispiel: 30 Gewichtsteile des Natriumsalzes des Azofarbstoffes aus diazotiertem 2,6-Dichlor- anilin und o-Kresol werden mit 23 Gewichts teilen methansulfinsaurem Natrium und 1500 Gewichtsteilen Wasser 6 Stunden im Druck gefäss auf<B>1550</B> C erhitzt.
Aus der Reaktions- lösung wird nach Filtrieren und Ausfällen mit verdünnter Säure ein Farbstoff abge schieden, welcher bei der Spaltung, beispiels weise mit Zinnchlorür, das 2-Amino-1,3-di- (methylsulfonyl)-benzol der folgenden Formel
EMI0001.0026
liefert. Die in der Literatur noch nicht beschrie bene Base kristallisiert aus verdünntem Al kohol in Blättchen, die bei<B>155</B> -157 C schmelzen. Die Analyse ergab folgende Werte: C 38,54,H 4,50, N 5,81, S 25,20. Die be rechneten Werte sind: C 38,51, H 4,44, N 5,62, S 25,73.
Process for the preparation of 2-amino-1,3-di- (methylsnlfonyl) -benzene. The subject of the present additional patent is a process for the production of 2-amino-1,3-di- (methylsulfonyl) -benzene, wel ches is characterized in that an alkali salt of the azotized by coupling of diacid 2,
6-dichloroaniline with o-gresol he available azo dye at elevated tempe temperature and under pressure with an alkali salt of methanesulfinic acid and the azo dye thus obtained splits by the action of a reducing agent.
The compound obtained is a valuable starting material, for example for the production of dyes.
Example: 30 parts by weight of the sodium salt of the azo dye from diazotized 2,6-dichloroaniline and o-cresol are heated to 1550 C for 6 hours in a pressure vessel with 23 parts by weight of sodium methanesulfinate and 1500 parts by weight of water.
After filtering and precipitating with dilute acid, a dye is separated from the reaction solution, which upon cleavage, for example with tin chloride, gives 2-amino-1,3-di (methylsulfonyl) benzene of the following formula
EMI0001.0026
supplies. The base, which has not yet been described in the literature, crystallizes from dilute alcohol in flakes that melt at 155 ° -157 ° C. The analysis gave the following values: C 38.54, H 4.50, N 5.81, S 25.20. The calculated values are: C 38.51, H 4.44, N 5.62, S 25.73.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE189028X | 1934-04-21 | ||
| CH183202T | 1935-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH189028A true CH189028A (en) | 1937-01-31 |
Family
ID=25720842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH189028D CH189028A (en) | 1934-04-21 | 1935-04-20 | Process for the preparation of 2-amino-1,3-di- (methylsulfonyl) -benzene. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH189028A (en) |
-
1935
- 1935-04-20 CH CH189028D patent/CH189028A/en unknown
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