CH209122A - Process for preparing a sulfonic acid amide compound. - Google Patents
Process for preparing a sulfonic acid amide compound.Info
- Publication number
- CH209122A CH209122A CH209122DA CH209122A CH 209122 A CH209122 A CH 209122A CH 209122D A CH209122D A CH 209122DA CH 209122 A CH209122 A CH 209122A
- Authority
- CH
- Switzerland
- Prior art keywords
- sulfonic acid
- methylbenzene
- methoxy
- preparing
- amide compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000013078 crystal Substances 0.000 claims description 5
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 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 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- -1 1-amino-2-methoxy-5-methylbenzene-4-sulfonic acid diethylamide Chemical compound 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- POLMNXCVMYMLSF-UHFFFAOYSA-N n-(2-methoxy-5-methylphenyl)acetamide Chemical compound COC1=CC=C(C)C=C1NC(C)=O POLMNXCVMYMLSF-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung einer Sulfonsäureamidverbindung Das Hauptpatent betrifft ein Verfahren zur Darstellung einer therapeutisch wert vollen Sulfonsäureamidverbiridung. Gegen stand des vorliegenden Patentes ist ein Ver fahren zur Darstellung einer Sulfonsäure- amidverbindung, dadurch gekennzeichnet, dass man 1-Acylamitio-2-metboxy-5-methylbenzol durch Einwirken von Chlorsulfonsäure in 1-Acylamirio-2-methoxy-5-methylbenzol-4-sul- fonsäurechlorid umwandelt,
dieses durch Ein wirken von Diäthylamin in 1-Acylamino-2- irietb oxy-5-inethyl b e nzol.4-s u 1 foris äuredi äthyl- amid umwandelt und aus diesem Produkt die Acylgruppe durch Verseifung abspaltet.
Das so erhältliche 1-Amino-2-niethoxy-5- metliylbenzol-4-sulfonsäurediäthylamid bildet farblose Kristalle vom Schmelzpunkt 124". Es soll therapeutische Anwendung finden. <I>Beispiel:</I> 100 g 1-Acetylamino-2-methoxy-5-methyl- benzol (aus Benzol weisse Kristalle vom Schmelzpunkt 112 0) werden bei 20 in 300 cm' Chlorsulfonsäure eingetragen. Die Mischung wird anschliessend 4 Stunden auf 70 o erhitzt. Sodann wird in Eiswasser ein gerührt und das ausgefällte 1-Acetylamino-2- methoxy-5-methylbenzol-4-sulforisäurechlorid abgesaugt.
Es bildet nach dem Umkristalli- sieren aus wässrigeni Aceton farblose Kristalle vom Schmelzpunkt 135 0. Zur Überführung in das Diäthylamid wird das von überschüs siger Mineralsäure durch Auswaschen befreite noch feuchte Chlorid mit 400 cm' Wasser und mindestens 2 Mol Diäthylamin ange- schlämmt und 30 Minuten bei 60-70 o ge rührt.
Nach dem Abkühlen wird das 1-Acetyl amino-2-metboxy-5-methylbenzol-4-sulfon- säurediäthylamid abgesaugt und durch Um- lbsen aus Natronlauge und Ammoniumchlorid gereinigt. 50 g dieser Verbindung werden mit 250 cms 20 /oiger Natronlauge unter Rühren gekocht. Aus der Mischung wird nachdem Erkalten das ausgefallene 1-Amino-2- methoxy-5-methylberizol-4-sul fonsäured i äthyl- amid abgesaugt.
Es bildet nach dem Um kristallisieren aus verdünntem Alkohol farb lose Kristalle vom Schmelzpunkt 1240.
Method for preparing a sulfonic acid amide compound The main patent relates to a method for preparing a therapeutically valuable sulfonic acid amide compound. The subject of the present patent is a process for the preparation of a sulfonic acid amide compound, characterized in that 1-acylamitio-2-metboxy-5-methylbenzene by the action of chlorosulfonic acid in 1-acylamirio-2-methoxy-5-methylbenzene-4 -sulfonic acid chloride converts,
this is converted into 1-acylamino-2-irietboxy-5-ynethylbenzol.4-s u 1 foris acid diethyl amide by the action of diethylamine and the acyl group is split off from this product by saponification.
The 1-amino-2-niethoxy-5-methylbenzene-4-sulfonic acid diethylamide which can be obtained in this way forms colorless crystals with a melting point of 124 ". It is intended to be used therapeutically. <I> Example: </I> 100 g of 1-acetylamino-2-methoxy -5-methylbenzene (white crystals from benzene with a melting point of 112 °) are introduced into 300 cm 'chlorosulfonic acid at 20 ° C. The mixture is then heated for 4 hours to 70 ° C. It is then stirred into ice water and the 1-acetylamino- 2- methoxy-5-methylbenzene-4-sulforic acid chloride suctioned off.
After recrystallization from aqueous acetone, it forms colorless crystals with a melting point of 135 0. For conversion into the diethylamide, the still moist chloride, freed from excess mineral acid by washing, is slurried with 400 cm of water and at least 2 mol of diethylamine and takes 30 minutes stirred at 60-70 o.
After cooling, the 1-acetyl amino-2-metboxy-5-methylbenzene-4-sulfonic acid diethylamide is filtered off with suction and purified by circulating sodium hydroxide solution and ammonium chloride. 50 g of this compound are boiled with 250 cms of 20% sodium hydroxide solution while stirring. After cooling, the precipitated 1-amino-2-methoxy-5-methylberizole-4-sulphonic acid i ethyl amide is suctioned off from the mixture.
After recrystallizing from dilute alcohol, it forms colorless crystals with a melting point of 1240.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE209122X | 1937-03-04 | ||
| CH203550T | 1938-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH209122A true CH209122A (en) | 1940-03-15 |
Family
ID=25723945
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209122D CH209122A (en) | 1937-03-04 | 1938-02-22 | Process for preparing a sulfonic acid amide compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH209122A (en) |
-
1938
- 1938-02-22 CH CH209122D patent/CH209122A/en unknown
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