AT223192B - Process for the preparation of substituted benzothiadiazine-1,1-dioxides - Google Patents
Process for the preparation of substituted benzothiadiazine-1,1-dioxidesInfo
- Publication number
- AT223192B AT223192B AT878559A AT878559A AT223192B AT 223192 B AT223192 B AT 223192B AT 878559 A AT878559 A AT 878559A AT 878559 A AT878559 A AT 878559A AT 223192 B AT223192 B AT 223192B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- dioxides
- benzothiadiazine
- formic acid
- substituted
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- UOCUSOBVEHOMMB-UHFFFAOYSA-N 2h-1$l^{6},2,3-benzothiadiazine 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)NN=CC2=C1 UOCUSOBVEHOMMB-UHFFFAOYSA-N 0.000 title 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- IHJCXVZDYSXXFT-UHFFFAOYSA-N chloraminophenamide Chemical compound NC1=CC(Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O IHJCXVZDYSXXFT-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- -1 orthoformic acid ester Chemical class 0.000 description 2
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical compound NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000008334 thiadiazines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Description
<Desc/Clms Page number 1>
EMI1.1
Die Herstellung von Thiadiazinverbindungen, im besonderen von substituierten Benzothiadiazin-1, 1dioxyden, erfolgt üblicherweise nach der Methode von Ekbom, Bihang till Svenska Vet. Akad. Handl., 27, 11, Nr. 1, 3 (1902). Das entsprechende o-Aminobenzolsulfonamid wird mit einem grossen Überschuss von Ameisensäure oder Orthoameisensäureester auf 100-150 C erhitzt. Nach beendeter Reaktion wird das Lösungsmittel durch Destillation entfernt. In der Kälte scheidet sich die gebildete Benzothiadiazinverbindung ab und wird aus Alkohol oder einem Alkohol-Wasser-Gemisch umkristallisiert.
Es wurde nun überraschend gefunden, dass die Herstellung von substituierten Benzothiadiazin-1, 1dioxyden der allgemeinen Formel I :
EMI1.2
EMI1.3
Verbindungen der allgemeinen Formel II :
EMI1.4
in welcher R die obige Bedeutung hat, mit Ameisensäure oder einem ameisensauren Salz auf sehr einfache Weise gelingt, wenn in Gegenwart von Schwefelsäure conc. bei Raumtemperatur gearbeitet wird.
Als Ausgangssubstanzen eignen sich besonders :
EMI1.5
Das erfindungsgemässe Verfahren wird durch die nachfolgenden Beispiele veranschaulicht, ohne es dadurch einzuschränken :
EMI1.6
<Desc / Clms Page number 1>
EMI1.1
Thiadiazine compounds, in particular substituted benzothiadiazine-1,1-dioxydes, are usually prepared by the method of Ekbom, Bihang till Svenska Vet. Akad. Handl., 27, 11, No. 1, 3 (1902). The corresponding o-aminobenzenesulfonamide is heated to 100-150 ° C. with a large excess of formic acid or orthoformic acid ester. After the reaction has ended, the solvent is removed by distillation. In the cold, the benzothiadiazine compound formed separates out and is recrystallized from alcohol or an alcohol-water mixture.
It has now surprisingly been found that the preparation of substituted benzothiadiazine-1,1-dioxydes of the general formula I:
EMI1.2
EMI1.3
Compounds of the general formula II:
EMI1.4
in which R has the above meaning, with formic acid or a formic acid salt succeeds in a very simple way if in the presence of sulfuric acid conc. is worked at room temperature.
The following are particularly suitable starting substances:
EMI1.5
The process according to the invention is illustrated by the following examples, without restricting it thereby:
EMI1.6
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT878559A AT223192B (en) | 1959-12-04 | 1959-12-04 | Process for the preparation of substituted benzothiadiazine-1,1-dioxides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT878559A AT223192B (en) | 1959-12-04 | 1959-12-04 | Process for the preparation of substituted benzothiadiazine-1,1-dioxides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT223192B true AT223192B (en) | 1962-09-10 |
Family
ID=3608491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT878559A AT223192B (en) | 1959-12-04 | 1959-12-04 | Process for the preparation of substituted benzothiadiazine-1,1-dioxides |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT223192B (en) |
-
1959
- 1959-12-04 AT AT878559A patent/AT223192B/en active
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