AT210876B - Process for the preparation of the new 2,4-disulfamyl-5-trifluoromethyl-aniline - Google Patents
Process for the preparation of the new 2,4-disulfamyl-5-trifluoromethyl-anilineInfo
- Publication number
- AT210876B AT210876B AT404059A AT404059A AT210876B AT 210876 B AT210876 B AT 210876B AT 404059 A AT404059 A AT 404059A AT 404059 A AT404059 A AT 404059A AT 210876 B AT210876 B AT 210876B
- Authority
- AT
- Austria
- Prior art keywords
- trifluoromethyl
- aniline
- new
- preparation
- disulfamyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- KRVABEGPNKGLOT-UHFFFAOYSA-N 4-amino-6-(trifluoromethyl)benzene-1,3-disulfonamide Chemical compound NC1=CC(C(F)(F)F)=C(S(N)(=O)=O)C=C1S(N)(=O)=O KRVABEGPNKGLOT-UHFFFAOYSA-N 0.000 title description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-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
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 4
- IDYGWCRGOWDFAM-UHFFFAOYSA-N 4-amino-6-(trifluoromethyl)benzene-1,3-disulfonyl chloride Chemical compound FC(C1=C(C=C(C(N)=C1)S(=O)(=O)Cl)S(=O)(=O)Cl)(F)F IDYGWCRGOWDFAM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 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 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 230000001452 natriuretic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung des neuen 2, 4-Disulfamyl-5-trifluormethyl-anilins
Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung des neuen 2, 4- Disulfarnyl-5-trifluormethyl-anilins der Formel :
EMI1.1
Diese Verbindung zeigt gegenüber vergleichbaren bekannten Verbindungen eine gute diuretische Wirksamkeit und kann vorteilhaft als Heilmittel Verwendung finden, z. B. in Form von pharmazeutischen Präparaten, welche diese Verbindung zusammen mit pharmazeutischen anorganischen oder organischen, festen oder flüssigen Trägerstoffen, die für enterale, z. B. orale, oder parenterale Verabreichung geeignet sind, enthalten. Sie ist ferner ein wertvolles Zwischenprodukt zur Herstellung von hochwirksamen Diuretika und/oder Natriuretika, wie z.
B. des 6- Triflourmethyl-7-sulfamyl-I, 2, 4-benzo- thiadiazin-l. l-dioxyds.
Die neue Verbindung lässt sich erhalten, wenn man 5-Trifluormethyl-anilin-2, 4-disulfonyl- chlorid mit Ammoniak, vorzugsweise mit einer wässerigen Ammoniaklösung, umsetzt. Dabei erhitzt man die Reaktionslösung vorzugsweise auf 1000 C.
Das als Ausgangsmaterial verwendete 5-Tri- fluormethyl-anilin-2,4-disulfonylchloridkann z.B. durch Erhitzen von 3- Trifluormethyl-anilin mit einem Überschuss Chlorsulfonsäure, gegebenenfalls in Gegenwart eines schwefelsäurebindenden oder Halogenierungsmittels, wie Kochsalz, Thionylchlorid, Sulfonylchlorid, Phosphortrichlorid, Phosphorpentachlorid, Tetrachlorkohlenstoff, Hexachloräthan oder Tetrachloräthylen, erhalten werden.
EMI1.2
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of the new 2,4-disulfamyl-5-trifluoromethyl-aniline
The present invention relates to a process for the preparation of the new 2,4-disulfarnyl-5-trifluoromethyl-aniline of the formula:
EMI1.1
This compound shows good diuretic activity compared to comparable known compounds and can advantageously be used as a medicinal product, e.g. B. in the form of pharmaceutical preparations, which this compound together with pharmaceutical inorganic or organic, solid or liquid carriers, which for enteral, z. B. oral, or parenteral administration are suitable included. It is also a valuable intermediate for the production of highly effective diuretics and / or natriuretics, such as.
B. 6-trifluoromethyl-7-sulfamyl-1,2,4-benzothiadiazine-1,2. l-dioxyds.
The new compound can be obtained if 5-trifluoromethyl-aniline-2,4-disulfonyl chloride is reacted with ammonia, preferably with an aqueous ammonia solution. The reaction solution is preferably heated to 1000 C.
The 5-trifluoromethyl-aniline-2,4-disulfonyl chloride used as starting material can e.g. by heating 3-trifluoromethyl-aniline with an excess of chlorosulfonic acid, optionally in the presence of a sulfuric acid-binding or halogenating agent such as common salt, thionyl chloride, sulfonyl chloride, phosphorus trichloride, phosphorus pentachloride, carbon tetrachloride, hexachloroethane or tetrachlorethylene.
EMI1.2
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US210876XA | 1957-12-13 | 1957-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT210876B true AT210876B (en) | 1960-08-25 |
Family
ID=21802273
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT404059A AT210876B (en) | 1957-12-13 | 1958-12-12 | Process for the preparation of the new 2,4-disulfamyl-5-trifluoromethyl-aniline |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT210876B (en) |
-
1958
- 1958-12-12 AT AT404059A patent/AT210876B/en active
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