CH229082A - Process for the preparation of a benzenesulfonamide derivative. - Google Patents
Process for the preparation of a benzenesulfonamide derivative.Info
- Publication number
- CH229082A CH229082A CH229082DA CH229082A CH 229082 A CH229082 A CH 229082A CH 229082D A CH229082D A CH 229082DA CH 229082 A CH229082 A CH 229082A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- reaction
- benzenesulfonamide derivative
- parts
- during
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000008331 benzenesulfonamides Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- RXNZFHIEDZEUQM-UHFFFAOYSA-N 2-bromo-1,3-thiazole Chemical compound BrC1=NC=CS1 RXNZFHIEDZEUQM-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- YZJXLVGCCTVYIH-UHFFFAOYSA-N NC1=CC=C(C=NS(=O)=O)C=C1 Chemical compound NC1=CC=C(C=NS(=O)=O)C=C1 YZJXLVGCCTVYIH-UHFFFAOYSA-N 0.000 description 1
- GKDDSBDRURXLKD-UHFFFAOYSA-N S(=O)(C1=CC=C(C=C1)N)(=O)N.[K] Chemical compound S(=O)(C1=CC=C(C=C1)N)(=O)N.[K] GKDDSBDRURXLKD-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
- C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines Benzolsulfonamidderivates. Geigenstand des vorliegenden Patentes bil- & t ein Verfahren zur Darstellung des im Patent Nr.
210425 beschriebenen Benzo,1sul- fonamid@derivates, welches dadurch gekenn zeichnet ist, dass man eine Verbindung der Formel
EMI0001.0014
worin X einen bei der Reaktion sieh abspal tenden Restbedeutet, auf ein 2-Ha.logen- thiazol einwirken lässt.
Die Reaktion wird zweckmässig in Gegen wart eines Katalysators undl'oder säurebin denden Mittels, wie z. B. Kupferpulver, ba- sisühen Mittelen, z. B. Alkalien wie Pottasche und dergleichen, in An- oder Abwesenheit von indifferenten Lösungsmitteln vorgenom men.
Das gebildete 2-(p-Aminobenzolsulfon- amido)-thiazol kann als solches .oder auch in Form .seiner Salze, z. B. ,des Natriums, Cal ciums .oder der Salzsäure, isoliert werden.
<I>Beispiel:</I> 26 Teile 2-Bromthiazol, 27 Teile p.-Amino- benzolsalfonamid, 22 Teile wasserfreie Pott asche und 1,5 Teile Kupferpulver werden innig miteinander vermengt und zunächst auf 175-180 erhitzt.
Nachdem die Real,-- tion etwas abgeklungen ist, wird die Tempe ratur noch eine Stunde auf etwa 200 gestei- gert. Nach -dem Erkalten wird das Reaktions- gemisth mit heissem Wasser behandelt und mit Norit filtriert. Durch Zusatz von Essig säure zum Filtrat wird das <RTI
ID="0001.0071"> 2-(p-Ami@noben- zol-s.ulfanami.do)-thiazo,1 in kristalliner Form ausgefällt. Nach dem Umkristallisieren aus verdünntem Alkohol erhält man es als weisse Substanz vom F. 202-203 .
Bei dieser Umsetzung bildet sich das Kaliumsalz des p.-Aminobenzolsulfonamids. Es kann .daher als Ausgangsstoff statt p- Aminobenzal.sulfonamid auch p-Aminobenzol- sulfonamidkalium verwendet werden.
Process for the preparation of a benzenesulfonamide derivative. Geigenstand of the present patent forms a method for the representation of the patent no.
210425 described benzo, 1sulfonamid @ derivates, which is characterized in that a compound of the formula
EMI0001.0014
where X denotes a residue that splits off during the reaction, allows a 2-halogenothiazole to act.
The reaction is expediently in the presence of a catalyst undl'oder säurebin Denden agent such. B. copper powder, basic agents, e.g. B. alkalis such as potash and the like, vorgenom men in the presence or absence of inert solvents.
The 2- (p-aminobenzenesulfonamido) -thiazole formed can be used as such .Or also in the form of. Its salts, e.g. B., of sodium, calcium. Or hydrochloric acid, are isolated.
<I> Example: </I> 26 parts of 2-bromothiazole, 27 parts of p-aminobenzenesalfonamide, 22 parts of anhydrous pot ash and 1.5 parts of copper powder are intimately mixed with one another and first heated to 175-180.
After the real tation has subsided somewhat, the temperature is increased to around 200 for another hour. After cooling, the reaction manure is treated with hot water and filtered with Norit. By adding acetic acid to the filtrate, the <RTI
ID = "0001.0071"> 2- (p-Ami @ noben- zol-s.ulfanami.do) -thiazo, 1 precipitated in crystalline form. After recrystallization from dilute alcohol, it is obtained as a white substance from F. 202-203.
During this reaction the potassium salt of p.-aminobenzenesulfonamide is formed. Therefore, instead of p-aminobenzal-sulfonamide, p-aminobenzene-sulfonamide potassium can also be used as the starting material.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH229082T | 1943-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH229082A true CH229082A (en) | 1943-09-30 |
Family
ID=4455905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH229082D CH229082A (en) | 1943-09-30 | 1938-09-16 | Process for the preparation of a benzenesulfonamide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH229082A (en) |
-
1938
- 1938-09-16 CH CH229082D patent/CH229082A/en unknown
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