CH314915A - Process for the preparation of 2-thiocyano-4: 6-diamino-s-triazine - Google Patents
Process for the preparation of 2-thiocyano-4: 6-diamino-s-triazineInfo
- Publication number
- CH314915A CH314915A CH314915DA CH314915A CH 314915 A CH314915 A CH 314915A CH 314915D A CH314915D A CH 314915DA CH 314915 A CH314915 A CH 314915A
- Authority
- CH
- Switzerland
- Prior art keywords
- triazine
- diamino
- preparation
- thiocyano
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 4
- 150000003918 triazines Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 239000000979 synthetic dye Substances 0.000 claims description 2
- 229920003002 synthetic resin Polymers 0.000 claims description 2
- 239000000057 synthetic resin Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
<B>Verfahren zur Herstellung von</B> 2-Thioeyano-4:6-diamino-s-triazin Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von 2-Thioeya.no- 4 : 6-diamino-s-tria.zin der Formel
EMI0001.0005
Das Verfahren ist dadurch gekennzeichnet, dass man Thiocyansäure mit 2-Chlor-4: 6- diamino-s-triazin in Wasser reagieren lässt, die entstehende Lösung neutralisiert und das ausgefällte Triazinderivat isoliert.
Das nachfolgende Beispiel soll. die Erfin dung näher erläutern: Beispiel 795 g Kaliumthiocyanat (2 Mol) werden in :500 ein- Wasser gelöst und 170 ein- Salz säure etwa 2 Mol HCl enthaltend, zwecks Bildung einer wässerigen Lösung von Thio- eyansäure zugefügt. Diese Lösung wird, um die Zersetzung möglichst zu vermeiden, in der Kälte (0-10 ) hergestellt und verwendet.
Zu dieser Lösung werden dann 25 g 2-Chlor-4:6- diamino-s-triazin (0,17 Mol) zugefügt, welches sieh rasch unter Bildung einer tiefroten Lö- sun@, auflöst. Die Lösung wird dann zwecks Entfernung geringer Mengen suspendierter Stoffe filtriert, worauf das Filtrat in der Kälte mit 20 0/aiger Natronlauge bis zu einem pA von etwa 5 neutralisiert wird.
Die hierbei entstehende gelbe Fällung (25 g = 90,51/0 der theoretischen Ausbeute) wird mit Aceton extrahiert, worin sie leicht löslich ist. Durch Verdampfen des Acetons wird das 2-Thio- eyano-4:6-diamino-s-triazin, frei von Chlor iden, erhalten.
Die neue Verbindung ist in Aceton leicht löslich und kann als Insektizid, als Anti- oxyda.ns und als Zwischenprodukt für die Herstellung von Triazin-Derivaten, synthe tischen Harzen, und Farbstoffen verwendet werden.
<B> Process for the preparation of </B> 2-Thioeyano-4: 6-diamino-s-triazine The present invention relates to a process for the preparation of 2-Thioeya.no-4: 6-diamino-s-triazine the formula
EMI0001.0005
The process is characterized in that thiocyanic acid is allowed to react with 2-chloro-4: 6-diamino-s-triazine in water, the resulting solution is neutralized and the precipitated triazine derivative is isolated.
The following example is supposed to. explain the invention in more detail: Example 795 g of potassium thiocyanate (2 mol) are dissolved in: 500 one-part water and 170 one-hydrochloric acid containing about 2 moles of HCl are added to form an aqueous solution of thioyanic acid. In order to avoid decomposition as much as possible, this solution is prepared and used in the cold (0-10).
25 g of 2-chloro-4: 6-diamino-s-triazine (0.17 mol) are then added to this solution, which dissolves rapidly with the formation of a deep red solution. The solution is then filtered to remove small amounts of suspended substances, whereupon the filtrate is neutralized in the cold with 20% sodium hydroxide solution to a pA of about 5.
The resulting yellow precipitate (25 g = 90.51 / 0 of the theoretical yield) is extracted with acetone, in which it is easily soluble. By evaporating the acetone, the 2-thioeyano-4: 6-diamino-s-triazine, free of chlorine ids, is obtained.
The new compound is easily soluble in acetone and can be used as an insecticide, as an antioxidant and as an intermediate for the manufacture of triazine derivatives, synthetic resins and dyes.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US314915XA | 1952-06-18 | 1952-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314915A true CH314915A (en) | 1956-07-15 |
Family
ID=21859751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314915D CH314915A (en) | 1952-06-18 | 1953-06-15 | Process for the preparation of 2-thiocyano-4: 6-diamino-s-triazine |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314915A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1111641B (en) * | 1958-07-24 | 1961-07-27 | Degussa | Process for the preparation of rhodantriazines |
-
1953
- 1953-06-15 CH CH314915D patent/CH314915A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1111641B (en) * | 1958-07-24 | 1961-07-27 | Degussa | Process for the preparation of rhodantriazines |
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