CH250004A - Process for the preparation of a benzenesulfonamide derivative. - Google Patents
Process for the preparation of a benzenesulfonamide derivative.Info
- Publication number
- CH250004A CH250004A CH250004DA CH250004A CH 250004 A CH250004 A CH 250004A CH 250004D A CH250004D A CH 250004DA CH 250004 A CH250004 A CH 250004A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- pyrazine
- methyl
- parts
- benzenesulfonamide derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000008331 benzenesulfonamides Chemical class 0.000 title claims description 3
- -1 2-benzenesulfonamido-6-methyl-pyrazine Chemical compound 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000565 sulfonamide group Chemical group 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UAOOJJPSCLNTOP-UHFFFAOYSA-N 6-methylpyrazin-2-amine Chemical compound CC1=CN=CC(N)=N1 UAOOJJPSCLNTOP-UHFFFAOYSA-N 0.000 description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KZPZWCOQVNUUPU-UHFFFAOYSA-N 4-amino-n-(6-methylpyrazin-2-yl)benzenesulfonamide Chemical compound CC1=CN=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 KZPZWCOQVNUUPU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical class CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 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
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
- C07D237/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/20—Nitrogen atoms
- C07D241/22—Benzenesulfonamido pyrazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Verfahren zur Herstellung eines Benzolsulfonamiddernvates- Gegenstand des vorliegenden Patentes ist Ein Verfahren zur Herstellung des im schweiz. Patent Nr. 244509 beschriebenen Benzolsulfonamidderivates, das dadurch ge kennzeichnet ist, dass man ein 2-Benzolsul- fonamido-6-methyl-pyrazin, das im Benzol ring in p-Stellung zur Sulfonamidgruppo einen durch Reduktion in die Aminogruppe überführbaren Substituenten aufweist,
mit einem reduzierenden Mittel behandelt.
Das 2 - Benzolsulfonamido - 6 - methyl- pyra.zin, das im Benzol.ring in p-Stellung zur Sulfonamidgruppe einen durch Reduk tion in die Aminogrup.pe überführbaren Substituenten enthält, kann auf verschiedene .Irt und Weise gewonnen werden.
Besonders geeignet ist die Umsetzung der entsprechen den reaktionsfähigen Benzolsulfonsäurederi- vate, insbesondere der Benzolsulfonsäure- halogenide, mit 6-Methyl-pyrazinverbindun- gen, die in 2-Stellung eine Gruppe enthal ten, die mit dem Benzolsulfonsäured-eri.vat ein 2-Benzolsulfonamido-6-methyl-pyrazin zu bilden vermag, insbesondere mit 2-Amino-6- methyl-pyrazin.Man kann aber auch entspre chende Sulfonamide der Formel RSOYHY,
in der Y einen bei der Reaktion sich abspal tenden Rest bedeutet, mit \2-Halogen-6- rnethyl-pyrazinen umsetzen oder andere dem Fachmann geläufige Herstellungsmethoden benutzen. <I>Beispiel:</I> Der Ausgangsstoff kann wie folgt her gestellt werden: 109 Teile 2 - Amino - 6 - methyl - pyrazin werden in 400 Teilen trockenem Pyridin ge löst und unter Rühren mit 221,5 Teilen p-Ni- tro-benzol:sulfochlorid in Portionen versetzt.
Man erwärmt 60 Minuten lang auf 95", destilliert das überschüssige Pyridin im Vakuum auf dem Wasserbad ab und versetzt den noch warmen Rückstand mit warmem Wasser. Man erhält Kristalle des 2-(Nitro- benzolsulfonamido)-6-methyl-pyrazins, die nach dem Erkalten abgenutscht, mit Wasser gewaschen und aus 50 % igem Alkohol um kristallisiert werden.
100 Teile vom Nutschkuchen trägt man in Portionen unter Rühren in die siedende Mischung von 200 Teilen feinem Eisen pulver, 100 Teilen 2n-Salzsäure und 1000 Teilen 50 % igem Alkohol. Nach beendetem Eintragen kocht man noch 4 Stunden am Rückfluss, destilliert den Alkohol ab, gibt Natronlauge zu, bis die Lösung stark auf Phenolphthalein reagiert, rührt<B>30</B> Minuten weiter und nutscht ab.
Aus dem Filtrat fällt man durch Neutralisation mit Salzsäure das 2 - (p - Amino - benzolsulf onamido) - 6 - methyl- pyrazin aus. Man kann aus 50 % igem Al kohol umkristallis$ren. F. 258-260 .
Das entstandene p - Amino - benzoIsulfon- amidderivat lässt sich auch in Form seiner Salze, z. B. des Natriums oder des Kalziums. isolieren.
Process for the production of a Benzolsulfonamiddernvates- the subject of the present patent is a process for the production of the in Switzerland. Patent No. 244509 described benzenesulfonamide derivative, which is characterized in that a 2-benzenesulfonamido-6-methyl-pyrazine, which in the benzene ring in the p-position to the sulfonamide group has a substituent which can be converted into the amino group by reduction,
treated with a reducing agent.
The 2-benzenesulfonamido-6-methylpyrazine, which in the benzene ring in the p-position to the sulfonamide group contains a substituent which can be converted into the amino group by reduction, can be obtained in various ways.
The reaction of the corresponding reactive benzenesulfonic acid derivatives, in particular the benzenesulfonic acid halides, with 6-methylpyrazine compounds which contain a group in the 2-position which, with the benzenesulfonic acid derivative, a 2-benzenesulfonamido, is particularly suitable -6-methyl-pyrazine is able to form, especially with 2-amino-6-methyl-pyrazine, but you can also use corresponding sulfonamides of the formula RSOYHY,
in which Y denotes a radical which splits off during the reaction, react with 2-halo-6-methylpyrazines or use other production methods familiar to the person skilled in the art. <I> Example: </I> The starting material can be prepared as follows: 109 parts of 2 - amino - 6 - methyl - pyrazine are dissolved in 400 parts of dry pyridine and mixed with 221.5 parts of p-nitro -benzene: sulfochloride mixed in portions.
The mixture is heated to 95 "for 60 minutes, the excess pyridine is distilled off in vacuo on the water bath and warm water is added to the still warm residue. Crystals of 2- (nitrobenzenesulfonamido) -6-methyl-pyrazine are obtained which, after the Sucked off to cool, washed with water and crystallized from 50% alcohol.
100 parts of the filter cake are carried in portions with stirring into the boiling mixture of 200 parts of fine iron powder, 100 parts of 2N hydrochloric acid and 1000 parts of 50% alcohol. After the end of the introduction, the mixture is refluxed for a further 4 hours, the alcohol is distilled off, sodium hydroxide solution is added until the solution reacts strongly to phenolphthalein, stirring is continued for 30 minutes and suction filtered.
The 2 - (p - amino - benzenesulfonamido) - 6 - methyl pyrazine is precipitated from the filtrate by neutralization with hydrochloric acid. You can recrystallize from 50% alcohol. F. 258-260.
The resulting p - amino - benzoIsulfon- amidderivat can also be used in the form of its salts, e.g. B. of sodium or calcium. isolate.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE250004X | 1939-05-23 | ||
| CH244346T | 1941-05-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH250004A true CH250004A (en) | 1947-07-31 |
Family
ID=25728932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH250004D CH250004A (en) | 1939-05-23 | 1941-05-23 | Process for the preparation of a benzenesulfonamide derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH250004A (en) |
-
1941
- 1941-05-23 CH CH250004D patent/CH250004A/en unknown
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