DE498747C - Process for the preparation of arylene thiazole disulfides - Google Patents
Process for the preparation of arylene thiazole disulfidesInfo
- Publication number
- DE498747C DE498747C DEI34057D DEI0034057D DE498747C DE 498747 C DE498747 C DE 498747C DE I34057 D DEI34057 D DE I34057D DE I0034057 D DEI0034057 D DE I0034057D DE 498747 C DE498747 C DE 498747C
- Authority
- DE
- Germany
- Prior art keywords
- disulfides
- preparation
- arylene
- percent
- thiazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 6
- -1 arylene thiazole disulfides Chemical class 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 150000002019 disulfides Chemical class 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- OZPDQKUEDLFNCO-UHFFFAOYSA-N 4,6-dimethyl-3h-1,3-benzothiazole-2-thione Chemical compound CC1=CC(C)=C2NC(=S)SC2=C1 OZPDQKUEDLFNCO-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- OIJDSGVKQAOWGO-UHFFFAOYSA-N cyclopenta[f][1,2]benzothiazine-2-thione Chemical compound SC=1C=C2C(=CC=C3C=CC=C32)SN1 OIJDSGVKQAOWGO-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/78—Sulfur atoms attached to a second hetero atom to a second sulphur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
Description
Verfahren zur Darstellung von Arylenthazoldisulfiden Es wurde gefunden, daß Arylmercaptothiazole der Formel: wobei der Arylrest substituiert oder unsubstituiert sein kann, sich in äußerst glatter Weise zu den entsprechenden Disulfiden oxydieren lassen, wenn man die Oxydation mit Hilfe von salpetriger Säure durchführt. Das Verfahren gestaltet sich technisch sehr einfach, indem man die Arylenmercaptothiazole in Form ihrer Alkalisalze unter Zusatz der erforderlichen Menge Nitrit in Wasser löst oder suspendiert und diese Lösungen bzw. Suspensionen in kalte verdünnte Mineralsäuren einlaufen läßt, wobei sich die Disulfide sofort abscheiden.Process for the preparation of arylene thazole disulfides It has been found that aryl mercaptothiazoles of the formula: where the aryl radical can be substituted or unsubstituted and can be oxidized to the corresponding disulfides in an extremely smooth manner if the oxidation is carried out with the aid of nitrous acid. The process is technically very simple by dissolving or suspending the arylene mercaptothiazoles in the form of their alkali salts with the addition of the required amount of nitrite and allowing these solutions or suspensions to run into cold, dilute mineral acids, the disulfides separating out immediately.
Der technische Vorteil dieses Verfahrens gegenüber den bisher bekannten Methoden (vgl. Ber. 2o [18871 S. 1790 und 21 [18881 S.2626) besteht darin, daß man mit einem billigen und sehr wirksamen Oxydationsmittel arbeiten kann und daß man die heterozyklischen Disulfide unmittelbar in reiner Form mit vorzüglicher Ausbeute erhält.The technical advantage of this process over the previously known Methods (cf. Ber. 2o [18871 p. 1790 and 21 [18881 p.2626) consists in that one can work with a cheap and very effective oxidizing agent and that one the heterocyclic disulfides directly in pure form with excellent yield receives.
Beispiel i 8,5 kg 2-Mercaptob,enzotMazol vom Schmelzpunkt 175° werden gelöst in ioo 1 Natronlauge (4prozentig) und ioo 1 einer Lösung von 7 kg Natriumnitrit in ioo 1 Wasser. Man läßt dann die Lösung bei Zimmertemperatur einlaufen in Zoo 1 4prozentige Salzsäure. Das abgesaugte Reaktionsprodukt zeigt, aus Butylalkohol umkristallisiert, den Schmelzpunkt i8o° und stimmt in seinen Eigenschaften mit dem von A. W. Hofman, Berichte 2o [i887] S. 1791 beschriebenen Disulfid überein.Example i 8.5 kg of 2-mercaptob, enzotMazol with a melting point of 175 ° dissolved in 100 1 sodium hydroxide solution (4 percent) and 100 1 of a solution of 7 kg sodium nitrite in 100 l of water. The solution is then allowed to run into Zoo at room temperature 1 4 percent hydrochloric acid. The suctioned off reaction product shows from butyl alcohol recrystallized, the melting point 180 ° and agrees in its properties with the by A. W. Hofman, Reports 20 [1887] p. 1791.
Beispiele 2 kg 2-Mercapto-4, 6-dimethylbenzothiazol werden in 2001 4prozentiger Natronlauge und 200 1 7prozentiger Natriumnitritlösung gelöst, und die Lösung bei Zimmertemperatur unter Rühren einlaufen lassen in 5001 4prozentige Salzsäure. Nach dem Absaugen zeigt das ausgeschiedene Disulfid, aus Butylalkohol umkristallisiert, den Schmelzpunkt 2o5°, während in der amerikanischen Patentschrift 1 635 193 ein solcher von 193° angegeben ist.Examples 2 kg of 2-mercapto-4,6-dimethylbenzothiazole are used in 2001 4 percent sodium hydroxide solution and 200 1 7 percent sodium nitrite solution dissolved, and let the solution run into 5001 4 percent at room temperature while stirring Hydrochloric acid. After the suction shows the precipitated disulfide, from butyl alcohol recrystallized, melting point 2o5 °, while in the American patent 1 635 193 is indicated as 193 °.
Beispiel 3 i,1 kg 2-Mercapto-6, 7-benzobenzthiazol werden mit Zoo 1 4prozentiger Natronlauge und 100 1 7prozentiger Natriumnitritlösung verrieben, und den geriebenen Kristallbrei des Natriummercaptids langsam unter Rühren einlaufen lassen in 300 1 4prozentige Salzsäure.EXAMPLE 3 1 kg of 2-mercapto-6,7-benzobenzothiazole are triturated with zoo 1 4 percent sodium hydroxide solution and 100 1 7 percent sodium nitrite solution, and the grated crystal pulp of the sodium mercaptide is slowly poured into 300 1 4 percent hydrochloric acid while stirring.
Man rührt noch % Stunde nach, saugt das Reaktionsprodukt ab und wäscht mit Wasser aus. Aus Chlorbenzol umkristallisiert erhält man das Disulfid in gelblichen Nadeln vom Schmelzpunkt 18-2 bis 1850.The mixture is stirred for a further ½ hour, and the reaction product is filtered off with suction and washed with water. Recrystallized from chlorobenzene, the disulfide is yellowish Needles from melting point 18-2 to 1850.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI34057D DE498747C (en) | 1928-04-04 | 1928-04-04 | Process for the preparation of arylene thiazole disulfides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI34057D DE498747C (en) | 1928-04-04 | 1928-04-04 | Process for the preparation of arylene thiazole disulfides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE498747C true DE498747C (en) | 1930-05-28 |
Family
ID=7188606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI34057D Expired DE498747C (en) | 1928-04-04 | 1928-04-04 | Process for the preparation of arylene thiazole disulfides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE498747C (en) |
-
1928
- 1928-04-04 DE DEI34057D patent/DE498747C/en not_active Expired
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