CH236177A - Process for the preparation of p-aminobenzenesulfonyl-propyl-thiourea. - Google Patents
Process for the preparation of p-aminobenzenesulfonyl-propyl-thiourea.Info
- Publication number
- CH236177A CH236177A CH236177DA CH236177A CH 236177 A CH236177 A CH 236177A CH 236177D A CH236177D A CH 236177DA CH 236177 A CH236177 A CH 236177A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- propyl
- aminobenzenesulfonyl
- thiourea
- mustard oil
- Prior art date
Links
- -1 p-aminobenzenesulfonyl-propyl-thiourea Chemical compound 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 2
- 239000008164 mustard oil Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 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 3
- 239000013078 crystal Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UHGKYJXJYJWDAM-UHFFFAOYSA-N Propylthiourea Chemical compound CCCNC(N)=S UHGKYJXJYJWDAM-UHFFFAOYSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- 239000003610 charcoal Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 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 1
- 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst 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
- 229940124530 sulfonamide Drugs 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)
Description
Verfahren zur Herstellung -von p-Aminobenzolsulfonyl-propyl-thioharnstoff. Im Hauptpatent ist ein Verfahren zur Her stellung von p-Aminobenzolsulfonyl-ä.thyl- thioharnstoff beschrieben, gemäss welchem man Athylsenföl auf Acetylsulfanilamid ein wirken lässt und den erhaltenen p-Acetyl- aminobenzolsulfonyl-äthylthiöharnstoff zum p - Aminobenzolsulfonyl - äthylthioharnstoff verseift.
Es wurde nun gefunden, dass man den p - Aminobenzolsulfonyl - propylthioharnstof f erhält, wenn man Propylsenföl auf Acetyl. sulfanilamid einwirken lässt und den erhalte nen p-Acetylaminobenzolsulfonyl-propylthio- harnstoff zum p-Aminobenzolsulfonyl-propy 1- thioharnstoff verseift.
Durch Gegenwart eines Katalysators kann wie beim Verfahren des Hauptpatentes die Umsetzung des .Senföls mit dem Sulfanil- a.midbeschleunigt werden.
Beispiel: 108 g Acetylsulfanilamid werden in einer Lösung von 2,0 g NaOH, 200 cm' H,0 und 200 cm' den. Alkohol gelöst. In der Lösung werden bei Zimmertemperatur unter Rühren 50 g P'ropylsenföl zugetropft. Es tritt geringe Temperaturerhöhung ein. Das Ganze wird Stunden bei gewöhnlicher Temperatur und 18 Stunden bei 50 gerührt.
Nach dem Ab kühlen wird mit 300 cm' H=0 verdünnt und der Alkohol im Vakuum bei 50 abdestilliert. Nach Behandlung mit Kohle wird die wäs serige Lösung durch konz. HCl kongosauer gemacht. Die abgesaugte und gewaschene aus fällte 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-propylthioharnstoff, wird abge saugt, mit Wasser gewaschen und getrocknet. Das Rohprodukt wird nicht weitergereinigt, sondern gleich zur entacetyliertenVerbindung weiterverarbeitet, indem 90 g der Acetylver- Bindung verseift werden. 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 63 g 1i- Aminobenzolsulfonyl-propylthioharnstoff als farblose Kristallnadeln vom h. 102-l05" er halten, die inWasser praktisch unlöslich sind. Sie lösen sich leicht in verdünnter Bicarbonat- lösung oder in verdünntem Ammoniak und werden aus solcher Lösung durch Essigsäur(, feinkristallinisch gefällt.
Process for the preparation of p-aminobenzenesulfonyl-propyl-thiourea. The main patent describes a process for the manufacture of p-aminobenzenesulfonyl-Ä.thyl 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 p - aminobenzenesulfonyl - propylthiourea is obtained when propyl mustard oil is added to acetyl. The sulfanilamide is allowed to act and the p-acetylaminobenzenesulfonylpropylthiourea obtained is saponified to form p-aminobenzenesulfonylpropy 1-thiourea.
By the presence of a catalyst, as in the process of the main patent, the reaction of mustard oil with sulfanil a.mide can be accelerated.
Example: 108 g of acetylsulfanilamide are dissolved in a solution of 2.0 g of NaOH, 200 cm H, 0 and 200 cm. Alcohol dissolved. 50 g propyl mustard oil are added dropwise to the solution at room temperature with stirring. There is a slight increase in temperature. The whole is stirred at ordinary temperature and 18 hours at 50 hours.
After cooling, it is diluted with 300 cm H = 0 and the alcohol is distilled off at 50 in vacuo. 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-acetylaminobenzenesulfonylpropylthiourea, is filtered off with suction, washed with water and dried. The crude product is not further purified, but immediately processed further 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 suction.
Washing and drying are 63 g of 1i-aminobenzenesulfonyl-propylthiourea as colorless crystal needles from the h. 102-105 ", which are practically insoluble in water. They dissolve easily in dilute bicarbonate solution or in dilute ammonia and are precipitated in fine crystalline form from such a solution by acetic acid (,.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE236177X | 1941-09-19 | ||
| CH229086T | 1942-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH236177A true CH236177A (en) | 1945-01-15 |
Family
ID=25727318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH236177D CH236177A (en) | 1941-09-19 | 1942-09-11 | Process for the preparation of p-aminobenzenesulfonyl-propyl-thiourea. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH236177A (en) |
-
1942
- 1942-09-11 CH CH236177D patent/CH236177A/en unknown
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