CH149314A - Process for the preparation of a nitrohaloquinazoline. - Google Patents
Process for the preparation of a nitrohaloquinazoline.Info
- Publication number
- CH149314A CH149314A CH149314DA CH149314A CH 149314 A CH149314 A CH 149314A CH 149314D A CH149314D A CH 149314DA CH 149314 A CH149314 A CH 149314A
- Authority
- CH
- Switzerland
- Prior art keywords
- nitro
- preparation
- oxy
- nitrohaloquinazoline
- weight
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 4
- WFUZYOKZUYVADR-UHFFFAOYSA-N 4-chloro-7-methyl-6-nitroquinazoline Chemical compound C1=NC(Cl)=C2C=C([N+]([O-])=O)C(C)=CC2=N1 WFUZYOKZUYVADR-UHFFFAOYSA-N 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical class ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 230000000973 chemotherapeutic effect Effects 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Verfahren zur Darstellung eines Nitroha.logenchinazolins. Iin Hauptpatent ist ein Verfahren zur Her stellung eines Nitrohälogenchinazolins be schrieben, dadurch gekennzeichnet, dass man auf 6-Nitro-4-oxychinazolin Phosphorchloride einwirken lässt.
Gegenstand vorliegender Erfindung ist nun ein Verfahren zur Herstellung eines Nitro- halogenchinazolins, dadurch gekennzeichnet, dass man 6-Nitro-4-oxy-7-metliylcbinazolin mit Phosphorchloriden behandelt.
<I>Beispiel:</I> a) 6-Nitro-4-oxy-7-metliylcliinazolin: 196 Gewichtsteile 5-Nitro-2-amino.-4-rnethylben- zoesäure (Nitrohomoanthranilsäure) werden mit 1000 Gewichtsteilen Formamid zunächst sechs Stunden auf 140-1501 erhitzt, hierbei geht die Nitrohomoanthranilsäure zunächst in Lösung; mit der Zeit erstarrt dann die Schmelze fast.
Sobald die Wasser- und Am moniakabspaltung träger wird, erhitzt man zur Vervollständigung der Reaktion noch zwei Stunden auf 170-1751. Die erkaltete Schmelze wird zur Entfernung des übei-scbüs- sigen Formamids mit Wasser ausgekocht. Das Ungelöste löst man in der eben nötigen Menge Natronlauge, und fällt das Natrium salz des 6-Nitro-4-oxy-7-iriethylchinazolius als gelbliche, undeutlich kristallisierte Verbindung aus.
Durch Salzsäure erhält man hieraus das 6-I\Titro-4-oxy-7-inethylchiriazolin. Es schmilzt bei<B>278';</B> aus Pyridin umkristallisiert bildet es gelbliche körnige Kristalle.
b) 6-Nitro-4-chlor-7-methylchinazolin: 205 Gewichtsteile obiger Verbindung werden mit 300 Cäewichtsteilen Phosphoroxychlorid an gerührt, dann gibt mau 210 Gewichtsteile Phosphorpentachlorid zu und erhitzt bei 120 bis 130" bis die Salzsäureabspaltung beendet ist.
Man destilliert hierauf zunächst im Va kuum der Wasserstrahlpumpe bei Wasserbad temperatur das 1'hospboi-oxychlorid, dann bei etwa<B>1900</B> das entstandene 6-Nitro-4-clilor- 7-methylchinazolin über. Es schmilzt bei 110 . In heissem Benzol und in- Aceton ist es leicht löslich.
Es soll als Zwischenprodukt zum Aufbau von Farbstoffen, pharmazeutischen und che motherapeutischen Präparaten und zu Mitteln zur Bekämpfung von Schädlingen Verwen dung finden.
Process for the preparation of a Nitroha.logenchinazoline. In the main patent, a process for the preparation of a nitrohalogenquinazoline is described, characterized in that phosphorus chlorides are allowed to act on 6-nitro-4-oxychinazoline.
The present invention now relates to a process for the preparation of a nitrohaloquinazoline, characterized in that 6-nitro-4-oxy-7-methylcbinazoline is treated with phosphorus chlorides.
<I> Example: </I> a) 6-Nitro-4-oxy-7-methylcliinazoline: 196 parts by weight of 5-nitro-2-amino.-4-methylbenzoic acid (nitrohomoanthranilic acid) are initially mixed with 1000 parts by weight of formamide for six hours heated to 140-1501, the nitrohomoanthranilic acid initially goes into solution; over time, the melt then almost solidifies.
As soon as the elimination of water and ammonia becomes sluggish, the mixture is heated to 170-1751 for two hours to complete the reaction. The cooled melt is boiled with water to remove the excess formamide. The undissolved material is dissolved in just the necessary amount of sodium hydroxide solution, and the sodium salt of 6-nitro-4-oxy-7-iriethylquinazolius precipitates as a yellowish, indistinctly crystallized compound.
Hydrochloric acid gives 6-I \ titro-4-oxy-7-ynethylchiriazoline from this. It melts at <B> 278 '; </B> Recrystallized from pyridine it forms yellowish, granular crystals.
b) 6-Nitro-4-chloro-7-methylquinazoline: 205 parts by weight of the above compound are stirred with 300 parts by weight of phosphorus oxychloride, then 210 parts by weight of phosphorus pentachloride are added and the mixture is heated at 120 to 130 "until hydrochloric acid has been split off.
The 1'hospboi-oxychloride is then distilled over first in the vacuum of the water-jet pump at water bath temperature, then the 6-nitro-4-chloro-7-methylquinazoline formed at about 1900. It melts at 110. It is easily soluble in hot benzene and in acetone.
It is intended to be used as an intermediate for the synthesis of dyes, pharmaceutical and chemotherapeutic preparations and as a means of combating pests.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE149314X | 1928-12-03 | ||
| CH145990T | 1929-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH149314A true CH149314A (en) | 1931-08-31 |
Family
ID=25714769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH149314D CH149314A (en) | 1928-12-03 | 1929-11-20 | Process for the preparation of a nitrohaloquinazoline. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH149314A (en) |
-
1929
- 1929-11-20 CH CH149314D patent/CH149314A/en unknown
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