CH236178A - Process for the preparation of p-aminobenzenesulfonyl-butylthiourea. - Google Patents
Process for the preparation of p-aminobenzenesulfonyl-butylthiourea.Info
- Publication number
- CH236178A CH236178A CH236178DA CH236178A CH 236178 A CH236178 A CH 236178A CH 236178D A CH236178D A CH 236178DA CH 236178 A CH236178 A CH 236178A
- Authority
- CH
- Switzerland
- Prior art keywords
- butylthiourea
- aminobenzenesulfonyl
- dissolve
- mustard oil
- acetylsulfanilamide
- Prior art date
Links
- -1 p-aminobenzenesulfonyl-butylthiourea Chemical compound 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- LIMQQADUEULBSO-UHFFFAOYSA-N butyl isothiocyanate Chemical compound CCCCN=C=S LIMQQADUEULBSO-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 238000005187 foaming Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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
- 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
- 239000008164 mustard oil Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 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
- 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
- 239000007864 aqueous solution 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
- 238000001914 filtration Methods 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
- 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-butylthioharnstoff. Im Hauptpatent ist ein Verfahren zur Her stellung von p-Aminobenzolsulfonyl-äthyl- tbioharnstoff 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 - butylthioharnstoff erhält, wenn man Butylsenföl auf Acetyl- sulfa.nilamid einwirken lässt und den entstan denen p-Acetylaminobenzolsulf onyl-butylthio- harnstoff zum p-Aminobenzolsulfonyl-butyl- thioharnstoff verseift.
Durch Gegenwart eines Katalysators kann wie beim Verfahren des Hauptpatentes die Umsetzung des Senföls mit dem Sulfanil- amid beschleunigt werden.
Beispiel: 108 g Acetylsulfanilamid werden in einer Lösung von 20 g Na0H, 200 cm' H20 und 200 cm' den. Alkohol gelöst. In der Lösung werden bei Zimmertemperatur unter Rühren 58g Butylsenföl zugetropft. Es tritt geringe Temperaturerhöhung ein. Das Ganze wird 2 Stunden bei gewöhnlicher Temperatur und 18 Stunden bei<B>50'</B> gerührt.
Nach dem Ab kühlen wird mit 300 cm' H20 verdünnt und der Alkohol im Vakuum bei<B>5,0'</B> 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 Wasser 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-butylthioharnstoff 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 58 g p-Amino- benzolsulfonyl-butylthioharnstoff als farb lose Kristalle vom F. 105-107 erhalten, die sich in Wasser nicht, dagegen ziemlich gut in Alkohol bei Erwärmen lösen.
In verdünnter Bicarbonat-, Soda- oder Ammoniaklösung lösen sie sich zu einer etwas schäumenden klaren Lösung auf, aus der sie durch Essig säure wieder ausgefällt werden.
Process for the preparation of p-aminobenzenesulfonyl-butylthiourea. The main patent describes a process for the manufacture of p-aminobenzenesulfonyl-ethyl-tbiourea, according to which ethyl mustard oil is allowed to act on acetylsulfanilamide and the resulting p-acetyl-aminobenzenesulfonyl-ethylthiourea becomes p-aminobenzenesulfonyl-ethylthiourea.
It has now been found that p-aminobenzenesulfonyl-butylthiourea is obtained if butyl mustard oil is allowed to act on acetylsulfa.nilamide and the resulting p-acetylaminobenzenesulfonyl-butylthiourea is saponified to p-aminobenzenesulfonyl-butylthiourea.
As in the process of the main patent, the reaction of the mustard oil with the sulfanilamide can be accelerated by the presence of a catalyst.
Example: 108 g of acetylsulfanilamide are dissolved in a solution of 20 g of NaOH, 200 cm H20 and 200 cm. Alcohol dissolved. 58 g of butyl mustard oil are added dropwise to the solution at room temperature with stirring. There is a slight increase in temperature. The whole is stirred for 2 hours at normal temperature and 18 hours at <B> 50 '</B>.
After cooling, it is diluted with 300 cm H20 and the alcohol is distilled off in vacuo at <B> 5.0 '</B>. 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-acetylaminobenzenesulfonylbutylthiourea, is filtered off with suction, washed with water and dried.
The crude product is not purified further, 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 filtering off with suction, washing and drying, 58 g of p-aminobenzenesulfonylbutylthiourea are obtained as colorless crystals of F. 105-107 which do not dissolve in water, but dissolve fairly well in alcohol when heated.
In dilute bicarbonate, soda or ammonia solution, they dissolve to a slightly foaming clear solution, from which they are precipitated again by acetic acid.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE236178X | 1941-09-19 | ||
| CH229086T | 1942-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH236178A true CH236178A (en) | 1945-01-15 |
Family
ID=25727319
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH236178D CH236178A (en) | 1941-09-19 | 1942-09-11 | Process for the preparation of p-aminobenzenesulfonyl-butylthiourea. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH236178A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2907692A (en) * | 1953-02-11 | 1959-10-06 | Boehringer & Soehne Gmbh | Composition for treating diabetes and a process of administering same |
-
1942
- 1942-09-11 CH CH236178D patent/CH236178A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2907692A (en) * | 1953-02-11 | 1959-10-06 | Boehringer & Soehne Gmbh | Composition for treating diabetes and a process of administering same |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH236177A (en) | Process for the preparation of p-aminobenzenesulfonyl-propyl-thiourea. | |
| CH236176A (en) | Process for the preparation of p-aminobenzenesulfonyl-allyl-thiourea. | |
| CH236179A (en) | Process for the preparation of p-aminobenzenesulfonyl-isoamylthiourea. | |
| CH282274A (en) | Process for the preparation of 2,9-dimethyl-1,10-phenanthroline. | |
| DE845347C (en) | Process for the preparation of pyridine-mercury compounds | |
| CH220970A (en) | Process for the preparation of a condensation product. | |
| CH220971A (en) | Process for the preparation of a condensation product. | |
| CH236175A (en) | Process for the preparation of p-aminobenzenesulfonyl-methyl-thiourea. | |
| CH245880A (en) | Process for the preparation of a new oxyhydrophenanthrene derivative. | |
| CH206091A (en) | Process for the preparation of a pseudonaphthazimide. | |
| CH252959A (en) | Process for the preparation of a new benzenesulfonylguanidine. | |
| CH112331A (en) | Process for the preparation of a new arsic acid. | |
| CH206090A (en) | Process for the preparation of a pseudonaphthazimide. | |
| CH122523A (en) | Process for the preparation of an aralkylamine. | |
| CH287867A (en) | Process for the preparation of 5-oxy-benz (cd) indoline. | |
| CH239155A (en) | Process for the production of a new benzene sulfonamide derivative. | |
| CH194683A (en) | Process for the preparation of sulfanilic acid 2-methyl-5-aminoanilide. | |
| CH199459A (en) | Process for the preparation of 4,4'-diisopropyl-6,6'-diaminostilbene-2,2'-disulfonic acid. | |
| CH217130A (en) | Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. | |
| CH199682A (en) | Process for the preparation of sulfanilic acid-4-aminoanilide. | |
| CH195466A (en) | Process for the preparation of sulfanilic acid-4-aminoanilide. | |
| CH245879A (en) | Process for the preparation of a new oxyhydrophenanthrene derivative. | |
| CH218270A (en) | Process for the preparation of a new methylene compound. | |
| CH243013A (en) | Process for the preparation of a p-amino-benzenesulfonacylamide. | |
| CH144988A (en) | Process for the preparation of p-glycolylaminobenzenic acid. |