CH237574A - Process for the preparation of 2-acetylamino-thiazole-5-sulfonanilide. - Google Patents
Process for the preparation of 2-acetylamino-thiazole-5-sulfonanilide.Info
- Publication number
- CH237574A CH237574A CH237574DA CH237574A CH 237574 A CH237574 A CH 237574A CH 237574D A CH237574D A CH 237574DA CH 237574 A CH237574 A CH 237574A
- Authority
- CH
- Switzerland
- Prior art keywords
- thiazole
- acetylamino
- sulfonanilide
- preparation
- soluble
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- LCFBSCJIFHTQFU-UHFFFAOYSA-N n-[5-(phenylsulfamoyl)-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC=C1S(=O)(=O)NC1=CC=CC=C1 LCFBSCJIFHTQFU-UHFFFAOYSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 241000534944 Thia Species 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 125000000565 sulfonamide group Chemical group 0.000 description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- -1 acetyl compound Chemical class 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Description
Verfahren zum Herstellen von 2-Acetylamino-thiazol-5o-sulfonanilid. Die bakteriziden Wirkungen von p-Amino- benzolsulfo#namid sind seit längerer Zeit bekannt, und es ist auch versucht worden, diese zur Bekämpfung bakterieller Infektio nen nutzbar zu machen.
Durch Änderungen dieses Körpers durch Substitution, insbeson dere in der Sulfonamidgruppe, sind Verbes serungen hinsichtlich der Wirksamkeit und Verträglichkeit erzielt worden, wobei sich insbesondere gezeigt hat, dass die Einführung des Pyridin- bezw. des Thiazolringes (2-SuJf- a.nilylaminGpyridin bezw. 2-Sulfanilylamina thiazol, günstig wirkt.
Es .sind awch 2-Amino- pyridin- bezw. -pyrimidin-5-sulfonamide her- ,gestellt worden, die ebenfalls bakterizide Eigenschaften zeigen. In a11 diesen Verbin dungen liegt als Grundkörper ein, Sechsring vor, in. welchem sich die Amino- und die Sul- fonamidgruppe in Pärastellung befinden.
Nach dem vorliegenden Verfahren wird eine neue Verbindung hergestellt, die als Grundkörper nicht einen Sechs-, sondern einen Fünfring, nämlich den Thiazolring enthält, in welchem sieh die Amino- und die Sulfonamidgruppe in 2-, 5-.Stellung gegen überstehen.
Trotz der von den vorstehend er wähnten bekannten Verbindungen abweichen- clen Struktur weist der neue .Stoff stark bak terizide Wirkungen auf; ausserdem sind in ihm die für eine chemotherapeutische Ver wendung erforderlichen Eigenschaften in günstiger Weise vereinigt. Die Verbindung zeichnet sich auch durch besonders gute Re sorptionsfähigkeit aus.
Erfindungsgemäss wird die neue Verbin- ,1ung, das 2-Acetylamino-tlliazol-5@-sulfonani- lid, hergestellt durch Umsetzen von acetylier- tem 2-Amino-thiazol-5-sulfochlorid mit Ani lin. Das 2-Acetylamino-thiazol-5-sulfonanilid hat den Zersetzungspunkt 272 . Es ist in Wasser schwer löslich, in Alkohol löslich, leicht löslich in Aceton, unlöslich in Benzol und Äther.
Das 2-Amino-thiazol kann nach Traumann ("Annalen der Chemie", Band 249, Seite 36) aus Dichloräthyläther und Thioharnstoff her gestellt werden. Es kann in Form seiner Ace- tylverbindung durch vorsichtige Behandlung mit Chlorsulfonsäure zum .Sulfochlorid um gesetzt werden, das als Ausgangsmaterial des vorliegenden Verfahrens dient. <I>Beispiel:</I> 1 g 2-Acetylamino-thiazol-5-sulfochlorid Lind 1 g Anilin werden in 5 ein- Aceton zu sammengebracht.
Nach Verdunsten des Ace tons wird der Rückstand mit VfTasser aus gezogen und das rohe 2-Acety la.mino-thiazol- 5-sulfonanilid aus 95 %igem Alkohol mit Tierkohle gereinigt. Farblose Nadeln, die sieh gegen 200 bräunen und bei 272-273 zer setze n.
Die erfindungsgemäss hergestellte Ver bindung soll als Heilmittel verwendet wer den.
Process for the preparation of 2-acetylamino-thiazole-5o-sulfonanilide. The bactericidal effects of p-aminobenzenesulfonamide have been known for a long time, and attempts have also been made to make them useful for combating bacterial infections.
By changes in this body through substitution, especially in the sulfonamide group, improvements in terms of effectiveness and tolerability have been achieved, and it has been shown in particular that the introduction of the pyridine or. of the thiazole ring (2-SuJf- a.nilylaminGpyridin or 2-sulfanilylamina thiazole, acts favorably.
It .sind awch 2-aminopyridine or. -pyrimidine-5-sulfonamides manufactured, which also show bactericidal properties. In a11 of these compounds there is a six-membered ring in which the amino and sulfonamide groups are in a pair.
According to the present process, a new compound is produced which contains not a six-membered ring, but a five-membered ring, namely the thiazole ring, in which the amino and sulfonamide groups are in the 2-, 5-.
In spite of the structure which differs from the known compounds mentioned above, the new substance has strong bactericidal effects; In addition, the properties required for chemotherapeutic use are advantageously combined in it. The connection is also characterized by particularly good absorption capacity.
According to the invention, the new compound, 2-acetylamino-tlliazole-5 @ -sulfonanilid, prepared by reacting acetylated 2-amino-thiazole-5-sulfochloride with aniline. The 2-acetylamino-thiazole 5-sulfonanilide has a decomposition point of 272. It is sparingly soluble in water, soluble in alcohol, easily soluble in acetone, insoluble in benzene and ether.
The 2-amino-thiazole can be made from dichloroethyl ether and thiourea according to Traumann ("Annalen der Chemie", Volume 249, page 36). In the form of its acetyl compound, careful treatment with chlorosulfonic acid can convert it to sulfochloride, which is used as the starting material for the present process. <I> Example: </I> 1 g of 2-acetylamino-thiazole-5-sulfochloride and 1 g of aniline are brought together in 5 units of acetone.
After the acetone has evaporated, the residue is drawn off with VfTasser and the crude 2-acetylamino-thiazole-5-sulfonanilide is purified from 95% alcohol with animal charcoal. Colorless needles that brown towards 200 and decompose at 272-273.
The compound produced according to the invention is intended to be used as a remedy to whoever.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE237574X | 1941-04-09 | ||
| CH231794T | 1942-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH237574A true CH237574A (en) | 1945-04-30 |
Family
ID=25727634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH237574D CH237574A (en) | 1941-04-09 | 1942-03-27 | Process for the preparation of 2-acetylamino-thiazole-5-sulfonanilide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH237574A (en) |
-
1942
- 1942-03-27 CH CH237574D patent/CH237574A/en unknown
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