DE209962C - - Google Patents
Info
- Publication number
- DE209962C DE209962C DENDAT209962D DE209962DA DE209962C DE 209962 C DE209962 C DE 209962C DE NDAT209962 D DENDAT209962 D DE NDAT209962D DE 209962D A DE209962D A DE 209962DA DE 209962 C DE209962 C DE 209962C
- Authority
- DE
- Germany
- Prior art keywords
- chloride
- catechol
- ber
- melting point
- water bath
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- YCIMNLLNPGFGHC-UHFFFAOYSA-N Catechol Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 9
- -1 catechol ethers Chemical class 0.000 claims description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K Aluminium chloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ABDKAPXRBAPSQN-UHFFFAOYSA-N 1,2-Dimethoxybenzene Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- RHZBRCQIKQUQHQ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetyl chloride Chemical compound C1=CC=C2C(=O)N(CC(=O)Cl)C(=O)C2=C1 RHZBRCQIKQUQHQ-UHFFFAOYSA-N 0.000 description 3
- QIAFMBKCNZACKA-UHFFFAOYSA-N Hippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- OZWUITKBAWTEAQ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)propanoic acid Chemical compound C1=CC=C2C(=O)N(C(C)C(O)=O)C(=O)C2=C1 OZWUITKBAWTEAQ-UHFFFAOYSA-N 0.000 description 1
- DXXHRZUOTPMGEH-UHFFFAOYSA-N 3-(1,3-dioxoisoindol-2-yl)propanoic acid Chemical compound C1=CC=C2C(=O)N(CCC(=O)O)C(=O)C2=C1 DXXHRZUOTPMGEH-UHFFFAOYSA-N 0.000 description 1
- 241001041510 Oxytelinae group Species 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000001919 adrenal Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
^ JVl 209962 KLASSE 12 o. GRUPPE^ JVl 209962 CLASS 12 o. GROUP
In der Patentschrift 185598, Kl. 120, ist ein Verfahren zur Darstellung von Hippurylbrenzkatechinalkyläthern beschrieben, die durch Kondensation von Hippursäurechlorid mit Brenzkatechinäthern erhalten werden.In the patent 185598, class 120, is a process for the preparation of Hippurylbrenzkatechinalkyläthern described by Condensation of hippuric acid chloride with catechol ethers can be obtained.
Es wurde nun gefunden, daß sich in weit besserer Ausbeute aus Phtalylglycylchlorid der Formel:It has now been found that the yield from phthalylglycyl chloride is far better Formula:
C H2- C O ClCH 2 - CO Cl
(Ber. 40, S. 2649) und Brenzkatechinäthern die Phtalimidoacetobrenzkatechinäther erhalten lassen, die ebenfalls wertvolle Zwischenprodukte für die Gewinnung von synthetischen Nebennierenpräparaten darstellen. Geht man bei dieser Reaktion von Homologen des Phtalylglycylchlorids aus, z. B. vom ß-Phtalimidopropionsäurechlorid (Phtalyl-ß-alanylchlorid) der Formel:(Ber. 40, p. 2649) and catechol ethers obtained the phtalimidoaceto catechol ethers let, which are also valuable intermediates for the production of synthetic adrenal preparations represent. If this reaction is based on homologues of phthalylglycyl chloride off, e.g. B. from ß-phthalimidopropionic acid chloride (phthalyl-ß-alanyl chloride) of Formula:
COsCOs
N-CH9-CH9-COClN-CH 9 -CH 9 -COCl
(Ber. 41, S. 242), so erhält man in ebenso glatter Ausbeute die entsprechenden anderen Phtalimidoverbindungen.(Ber. 41, p. 242), one also obtains in the corresponding other phthalimido compounds in a smooth yield.
40 g Phtalylglycylchlorid (Ber. 40, S. 2649), 40 g Veratrol und 40 g Aluminiumchlorid werden eine halbe Stunde' auf dem Wasserbade erwärmt, bis die anfangs stürmische Salzsäureentwicklung vorüber ist. Dann wird zunächst mit etwas Eis und verdünnter Salzsäure versetzt, zur vollständigen Zersetzung kurze Zeit im Wasserbade erwärmt und schließlich unverändertes Veratrol mit Dampf abgeblasen. Der Rückstand wird mit etwas Alkohol verrieben, abgesaugt und zur Reinigung zweimal mit einem halben Liter Alkohol ausgekocht. Das Phtalimidoacetoveratrol bleibt als weißes Pulver vom Schmelzpunkt 2020 zurück. Ausbeute 40 bis 50 g.40 g of phthalylglycyl chloride (Ber. 40, p. 2649), 40 g of veratrole and 40 g of aluminum chloride are heated on the water bath for half an hour until the initially stormy evolution of hydrochloric acid has passed. Then a little ice and dilute hydrochloric acid are first added, heated for a short time in a water bath for complete decomposition and finally unchanged veratrole is blown off with steam. The residue is triturated with a little alcohol, filtered off with suction and boiled twice with half a liter of alcohol for cleaning. The Phtalimidoacetoveratrol remains as a white powder of melting point 202 0th Yield 40 to 50 g.
44 g trockene α - Phtalimidopropionsäure (Phtalyl-a-alanin) vom Schmelzpunkt 160 bis 1620 (Ber. 38, S. 634) werden mit 42 g Phosphorpentachlorid im Wasserbade bis zur Lösung erwärmt, dann wird Phosphoroxychlorid im Vakuum abdestilliert und der Rückstand aus Ligroin umkristallisiert. Man erhält so das a-Phtalimidopropionsäurechlorid in weißen Kristallen vom Schmelzpunkt 710.44 g of dry α - phthalimidopropionic acid (phthalyl-a-alanine) with a melting point of 160 to 162 0 (Ber. 38, p. 634) are heated to solution with 42 g of phosphorus pentachloride in a water bath, then phosphorus oxychloride is distilled off in vacuo and the residue is removed Ligroin recrystallized. Is obtained as the a-Phtalimidopropionsäurechlorid in white crystals of melting point 71 0th
Zur Kondensation werden "50 g Chlorid mit 50 g Veratrol auf dem Wasserbade geschmolzen und in die etwas erkaltete Mischung 50 g gepulvertes Äluminiumchlorid eingetragen. Es tritt bald lebhafte Reaktion ein, die durch Erwärmen auf dem Wasserbade (etwa 20 Minuten) beendet wird. Nach dem Zersetzen mit Eiswasser und verdünnter Salzsäure wird unverändertes Veratrol mit Dampf abgeblasen und der Rückstand durch Aufkochen mitFor condensation, "50 g of chloride are melted with 50 g of veratrole on the water bath and added 50 g of powdered aluminum chloride to the somewhat cooled mixture. It vigorous reaction soon occurs, which can be achieved by warming up on the water bath (about 20 minutes) is terminated. After decomposition with ice water and dilute hydrochloric acid, unchanged veratrole is blown off with steam and the residue by boiling with
Alkohol gereinigt. Das ct-Phtalimidopropionylveratrol bleibt als weißes Pulver vom Schmelzpunkt 212° zurück.Alcohol cleaned. The ct-phthalimidopropionylveratrol remains as a white powder with a melting point of 212 °.
Man kann auch das nach dem Abdestillieren des Phosphoroxychlorids erhaltene rohe Chlorid direkt weiter verarbeiten.The crude chloride obtained after the phosphorus oxychloride has been distilled off can also be used further process directly.
Analog wurde aus dem ß-Phtalimidopropionsäurechlorid (Ber. 41, S. 242) das ß-Phtalimidopropionveratrol erhalten, das aus Alkohol in weißen glänzenden Blättchen vom Schmelzpunkt 1750 kristallisiert.Analog was obtained from the ß-Phtalimidopropionsäurechlorid (Ber. 41, p 242) the SS Phtalimidopropionveratrol which crystallizes from alcohol in lustrous white flakes of melting point 175 0th
Statt Veratrol können auch andere Äther des Brenzkatechins, wie Diäthylbrenzkatechin, oder es können andere als die erwähnten Chloride von Phtalimidofettsäuren verwendet werden.Instead of Veratrol, other ethers of catechol, such as diethyl catechol, can also be used. or chlorides of phthalimido fatty acids other than those mentioned can be used will.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE209962C true DE209962C (en) |
Family
ID=471890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT209962D Active DE209962C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE209962C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5741178A (en) * | 1994-12-09 | 1998-04-21 | Binks Manufacturing Company | Reducing area, increasing velocity paint booth structure and method |
-
0
- DE DENDAT209962D patent/DE209962C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5741178A (en) * | 1994-12-09 | 1998-04-21 | Binks Manufacturing Company | Reducing area, increasing velocity paint booth structure and method |
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