CH236176A - Process for the preparation of p-aminobenzenesulfonyl-allyl-thiourea. - Google Patents
Process for the preparation of p-aminobenzenesulfonyl-allyl-thiourea.Info
- Publication number
- CH236176A CH236176A CH236176DA CH236176A CH 236176 A CH236176 A CH 236176A CH 236176D A CH236176D A CH 236176DA CH 236176 A CH236176 A CH 236176A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminobenzenesulfonyl
- allyl
- thiourea
- allylthiourea
- acetylsulfanilamide
- Prior art date
Links
- 229960001748 allylthiourea Drugs 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 claims description 9
- PKOFBDHYTMYVGJ-UHFFFAOYSA-N n-(4-sulfamoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S(N)(=O)=O)C=C1 PKOFBDHYTMYVGJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SVVWVJVDFDKKCG-UHFFFAOYSA-N CCN(C(N)=S)S(C(C=C1)=CC=C1N)(=O)=O Chemical compound CCN(C(N)=S)S(C(C=C1)=CC=C1N)(=O)=O SVVWVJVDFDKKCG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- -1 ethyl mustard oil Chemical compound 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000008164 mustard oil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YZVJSEKTVIWOPD-UHFFFAOYSA-N CCN(C(NN)=S)S(C(C=C1)=CC=C1C(C)=O)(=O)=O Chemical compound CCN(C(NN)=S)S(C(C=C1)=CC=C1C(C)=O)(=O)=O YZVJSEKTVIWOPD-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 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
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung von p-Aminobenzolsulfonyl-allyl-thioharnstoff. Im Hauptpatent ist ein Verfahren zur Her stellung von p - Aminobenzolsulfonyl - äthyl- thioharnstoff beschrieben, gemäss welchem man Äthylsenföl auf Acetylsulfanilamid ein wirken lässt und den erhaltenen p-Acetyl- aminobenzolsulfonyl-äthylthioharnstoff zum p - Aminobenzolsulfonyl - äthylthioharnstoff verseift.
Es wurde nun gefunden, dass man den p - Aminobenzolsulfonyl - allylthioharnstoff erhält, wenn man Allylsenföl auf Acetyl- sulfanilamid einwirken lässt und den erhalte nen p-Acetylaminobenzolsulfonyl-allylthio- harnstoff zum p-Aminobenzolsulfonyl-allyl- thioharnstoff verseift.
Durch Gegenwart eines Katalysators kann wie beim Verfahren des Hauptpatentes die Umsetzung des -Senföls mit dem Sulfanil.. timid beschleunigt werden.
<I>Beispiel:</I> 108 g Acetylsulfanilamid werden in einer Lösung von 20g NaOH, 200 cm' H20 und 200 cm' den. Alkohol gelöst. In der Lösung Urerden bei Zimmertemperatur unter Rühren 50 g Allylsenföl zugetropft. Es tritt geringe Temperaturerhöhung ein. Das Ganze wird 2 Stunden bei gewöhnlicher Temperatur und 18 Stunden bei 509 gerührt.
Nach dem Ab kühlen wird mit<B>300</B> cm'<B>11,0</B> verdünnt und der Alkohol im Vakuum bei 509 abdestilliert. Nach Behandlung mit Kohle wird die wäs serige Lösung durch konz. HCl kongosauer gemacht. Die abgesaugte und gewaschene aus gefällte Substanz wird gut pulverisiert und 1-2 Stunden mit überschüssigem Natrium bikarbonat und Wassser gerührt.
Nach Ab saugen von ungelöstem Ausgangsmaterial wird das Filtrat unter Rühren in überschüs sige Eisessiglösung (1 : 1) eingetropft. Die ausgefällte Substanz, der p-Acetylaminoben- zolsulfonyl-allylthioharnstoff wird abgesaugt, mit Wasser gewaschen und getrocknet. Das Rohprodukt wird"nicht weitergereinigt, son dern gleich zur entacetylierten Verbindung weiterverarbeitet, indem man 90g der Acetyl- verbindung verseift.
Das zuerst erhaltene Kaliumsalz wird in Wasser gelöst, die Lö sung mit Kohle entfärbt und die farblose Lösung unter Rühren in überschüssige Eis essiglösung 1 : 1 eingetropft. Nach Absaugen, Waschen und Trocknen werden zirka 70 g p-Aminobenzolsulfonyl-allylthioharnstoff er halten, der feine weisse Nadeln vom E. P. 115 bis 116<B>'</B> bildet. Der neue Endstoff ist zur Verwendung für therapeutische Zwecke be stimmt.
Process for the preparation of p-aminobenzenesulfonyl-allyl-thiourea. The main patent describes a process for the manufacture of p - aminobenzenesulfonyl - ethyl thiourea, according to which ethyl mustard oil is allowed to act on acetylsulfanilamide and the resulting p-acetyl aminobenzenesulfonyl-ethylthiourea to p - aminobenzenesulfonyl - ethylthiourea.
It has now been found that the p-aminobenzenesulfonyl-allylthiourea is obtained when allyl mustard oil is allowed to act on acetylsulfanilamide and the p-acetylaminobenzenesulfonyl-allylthiourea obtained is saponified to give p-aminobenzenesulfonyl-allyl-thiourea.
By the presence of a catalyst, as in the process of the main patent, the reaction of the mustard oil with the sulfanil .. timid can be accelerated.
<I> Example: </I> 108 g of acetylsulfanilamide are dissolved in a solution of 20 g of NaOH, 200 cm 'H20 and 200 cm' den. Alcohol dissolved. 50 g of allyl mustard oil were added dropwise to the Urerden solution at room temperature with stirring. There is a slight increase in temperature. The whole is stirred for 2 hours at ordinary temperature and 18 hours at 509.
After cooling, it is diluted with <B> 300 </B> cm '<B> 11.0 </B> and the alcohol is distilled off in vacuo at 509. After treatment with charcoal, the aqueous solution is concentrated by conc. HCl made Congo acidic. The filtered off and washed precipitated substance is pulverized well and stirred for 1-2 hours with excess sodium bicarbonate and water.
After undissolved starting material has been sucked off, the filtrate is added dropwise to excess glacial acetic acid solution (1: 1) with stirring. The precipitated substance, the p-acetylaminobenzenesulfonyl-allylthiourea, is filtered off with suction, washed with water and dried. The crude product is "not further purified, but processed straight away to give the deacetylated compound by saponifying 90 g of the acetyl compound.
The potassium salt obtained first is dissolved in water, the solution is decolored with charcoal and the colorless solution is added dropwise to excess glacial acetic acid solution 1: 1 with stirring. After suctioning off, washing and drying, about 70 g of p-aminobenzenesulfonyl-allylthiourea are obtained, which forms fine white needles from E.P. 115 to 116 <B> '</B>. The new end product is intended to be used for therapeutic purposes.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE236176X | 1941-09-19 | ||
| CH229086T | 1942-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH236176A true CH236176A (en) | 1945-01-15 |
Family
ID=25727317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH236176D CH236176A (en) | 1941-09-19 | 1942-09-11 | Process for the preparation of p-aminobenzenesulfonyl-allyl-thiourea. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH236176A (en) |
-
1942
- 1942-09-11 CH CH236176D patent/CH236176A/en unknown
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