DE1670752A1 - Process for the preparation of 2-phenylamino-oxazolines - Google Patents
Process for the preparation of 2-phenylamino-oxazolinesInfo
- Publication number
- DE1670752A1 DE1670752A1 DE19661670752 DE1670752A DE1670752A1 DE 1670752 A1 DE1670752 A1 DE 1670752A1 DE 19661670752 DE19661670752 DE 19661670752 DE 1670752 A DE1670752 A DE 1670752A DE 1670752 A1 DE1670752 A1 DE 1670752A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- group
- halogen
- phenylamino
- alkyl group
- 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.)
- Pending
Links
- CIDMUJMGDBSMQW-UHFFFAOYSA-N n-phenyl-4,5-dihydro-1,3-oxazol-2-amine Chemical class O1CCN=C1NC1=CC=CC=C1 CIDMUJMGDBSMQW-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- -1 chlorine or bromine Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical compound Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- RCIBIGQXGCBBCT-UHFFFAOYSA-N phenyl isocyanide Chemical compound [C-]#[N+]C1=CC=CC=C1 RCIBIGQXGCBBCT-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- PSYZOOOPACOKKZ-UHFFFAOYSA-N 1-(2-chloroethyl)-3-(2-methoxy-6-methylphenyl)urea Chemical compound COC1=CC=CC(C)=C1NC(=O)NCCCl PSYZOOOPACOKKZ-UHFFFAOYSA-N 0.000 description 1
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
- MGYAGUUKOYNYAT-UHFFFAOYSA-N 2-(oxan-2-yl)oxane Chemical compound O1CCCCC1C1OCCCC1 MGYAGUUKOYNYAT-UHFFFAOYSA-N 0.000 description 1
- VINFKVPYBSPVPP-UHFFFAOYSA-N 2-isocyano-1-methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1[N+]#[C-] VINFKVPYBSPVPP-UHFFFAOYSA-N 0.000 description 1
- HKOJYPPTIPJZAZ-UHFFFAOYSA-N 2-methoxy-6-methylaniline Chemical compound COC1=CC=CC(C)=C1N HKOJYPPTIPJZAZ-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/28—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
LEVERKU S EN-Beyerwerk 11. November 1969 P 16 70 752.1 P«ent-Abteilung Si/ScLEVERKU S EN-Beyerwerk November 11, 1969 P 16 70 752.1 P «ent department Si / Sc
Verfahren zur Herstellung von 2-Phenylamino-oxazolinenProcess for the preparation of 2-phenylamino-oxazolines
Es wurde gefunden, daß 2-Phenylamino-2-oxazoline der allgemeinen FormelIt has been found that 2-phenylamino-2-oxazolines are of the general formula
in derin the
R eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen, eine Alkoxygruppe mit 1 bis 4 Kohlenstoffatomen, oder Halogen, wie Chlor oder Brom,R is an alkyl group with 1 to 4 carbon atoms, an alkoxy group with 1 to 4 carbon atoms, or halogen, such as chlorine or bromine,
R1 eine Methyl- oder eine ithylgruppe undR 1 is a methyl or an ithyl group and
R" Wasserstoff, eine Alkylgruppe mit 1 bis 4 Kohlenstoffatomen, ein© Alkoxygruppe mit 1 bis 4 Kohlenstoffatomen oder eine Aeylgruppe mit 1 bis 4 Kohlenstoffatomen oder Halogen bedeuten,R "hydrogen, an alkyl group with 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or an ayl group having 1 to 4 carbon atoms or halogen mean
ausgeprägte pharmakodynamische Aktivität besitzen«have pronounced pharmacodynamic activity "
Von 2-Aminooxasolinen sind bisher lokalanästhetische, sedative und vasoconstrictorische Wirkungen (Anwendung zur Schleimhautabschwellung) bekannt geworden. Über dieseSo far, 2-Aminooxasolinen are local anesthetic, sedative and vasoconstrictor effects (application to decongest the swelling of the mucous membrane) have become known. About these
Le A 10 278Le A 10 278
' 009852/atSO'009852 / atSO
Wirkungen hinaus entfalten die erfindungsgemäß hergestellten Substanzen eine starke blutdrucksenkende Wirkung und eine hemmende Wirkung auf die MagensaftSekretion. Sie sind daher wertvoll zur Behandlung verschiedener Hypertonieformen und eur*Behandlung des Ulcus. Ferner kann ein Teil dieser Verbindungen wegen ihrer blutzuckersteigernden Aktivität bei bestimmten Erkrankungen in der Human- und Veterinärmedizin Verwendung finden.In addition to effects, the substances produced according to the invention develop a strong antihypertensive effect and a inhibitory effect on gastric juice secretion. You are therefore Valuable for the treatment of various forms of hypertension and eur * treatment of the ulcer. Furthermore, some of these compounds because of their blood sugar-increasing activity in certain diseases in human and veterinary medicine Find use.
Die Herstellung der genannten 2-Phenylaminooxazoline erfolgt erfindungsgemäß dadurch, daß man entweder Phenylisocyaniddichloride der allgemeinen FormelThe aforementioned 2-phenylaminooxazolines are produced according to the invention in that either phenyl isocyanide dichlorides the general formula
in derin the
R1 E1 R 1 E 1
und R" die obengenannte Bedeutung besitzen,and R "have the meaning given above,
mit Äthanolamin in organischen Lösungsmitteln oder in Wasser, gegebenenfalls unter Zusatz von Basen, wie Triäthylamin, W Kaliumcarbonat oder Natriumhydroxid bei O bis 10O0O umsetzt, oder daß man reaktionsfähige Ester von Alkoholen der allgemeinen Formelwith ethanolamine in organic solvents or in water, optionally with addition of bases, such as triethylamine, potassium carbonate or sodium hydroxide at O W reacted to 10O 0 O, or in that reactive esters of alcohols of the general formula
HH-CO-HH-CH2-CH2Oh RHH-CO-HH-CH 2 -CH 2 Oh R
in derin the
R, R!R, R!
und Rn die obengenannte Bedeutung besitzen,and R n have the meaning given above,
Le A 10 278 - 2 - Le A 10 278 - 2 -
009852/2190009852/2190
durch Erhitzen in Wasser, gegebenenfalls bei Temperaturen oberhalb 10O0C, unter Druck cyclisiert. Die so erhaltenen Salze können gegebenenfalls mit Basenf wie Natronlauge oder Ammoniak, in die freien Basen überführt werden.cyclized by heating in water, optionally at temperatures above 10O 0 C, under pressure. The salts thus obtained can, if appropriate, f with bases such as sodium hydroxide or ammonia, are converted into the free bases.
Die reaktionsfähigen Ester aer obengenannten Alkohole erhält man nach an sich bekannten Verfahren durch Umsetzung von Aminen der FormelThe reactive esters of the abovementioned alcohols are obtained by processes known per se by reacting amines of the formula
in derin the
und R" die obenangegebene Bedeutung besitzen,and R "have the meaning given above,
mit ß-Halogenäthylisocyanaten oder durch Umsetzung von substituierten Phenylisocyanaten der Formelwith ß-Halogenäthylisocyanaten or by reacting substituted phenyl isocyanates of the formula
in derin the
und R" die obenangegebene Bedeutung besitzen,and R "have the meaning given above,
mit Aminoäthanol und nachfolgende Einwirkung von Thionylhalogeniden. Anstelle von Thionylhalogeniden lassen sich auch SuIfonylhalogenide wie Methansulfonylchlorid oder p-Toluolsulfochlorid verwenden. Es entstehen dann in Gegenwart tertiärer Basen die Sulfonsäureester der obengenannten Alkohole.with aminoethanol and subsequent exposure to thionyl halides. Instead of thionyl halides, sulfonyl halides such as methanesulfonyl chloride or Use p-toluenesulfonyl chloride. They then arise in the present tertiary bases, the sulfonic acid esters of the alcohols mentioned above.
Ie A 10 278 - 3 - Ie A 10 278 - 3 -
0098527219000985272190
Bei dieser Arbeitsweise ist. es nicht notwendig, die ein-2elnen Zwischenstufen zu isolieren. Man kann beispielsweise direkt von substituierten Phenylisocyaiiaten ausgehen und erhält durch successive Umsetzung mitIn this way of working. it is not necessary to isolate the individual intermediate stages. One can for example start directly from substituted Phenylisocyaiiaten and get by successive reaction with
a) Äthanolamina) ethanolamine
bj Thionylchloridbj thionyl chloride
c) Erhitzen in Wasserc) heating in water
die gewünschten substituierten 2-Phenylamino-2-oxazoline. Die als Ausgangsmaterial erwähnten Isocyaniddichloride werden z. B. durch Chloranlagerung an entsprechende substi- * tuierte Phenylisonitrile gewonnen.^the desired substituted 2-phenylamino-2-oxazolines. The isocyanide dichlorides mentioned as starting material are z. B. by adding chlorine to corresponding substi- * tuated phenylisonitrile obtained. ^
Die nach dem obengenannten Verfahren hergestellten substituierten Phenylamino-2-oxazoline können auch in ihrer tautomeren Form als 2-Phenylimino-oxazolidine vorliegen.The substituted ones prepared by the above process Phenylamino-2-oxazoline can also be tautomeric in their In the form of 2-phenylimino-oxazolidines.
Sie stellen meistens gut kristallisierende Basen dar, die sich mit Säuren in kristallisiertet meist leicht lösliche Salze überführen lassen. Besonders geeignet dazu sind die Säuren schwacher anorganischer oder organischer Säuren, wie Phosphorsäure! Essigsäure, Milchsäure, Fumarsäure, Bernsteinsäure und Weinsäure.They usually represent bases that crystallize well, the with acids crystallized in mostly easily soluble ones Let the salts transfer. The Acids of weak inorganic or organic acids, such as phosphoric acid! Acetic acid, lactic acid, fumaric acid, succinic acid and tartaric acid.
Eine Suspension von 21,3 g H-(2-Methoxy-6-methylphenyl)-N·- (ß-chloräthy 1)-harnstoff in 250 ml Wasser wird unter kräftigem Rühren 45 Minuten unter Rückfluß erhitzt. Nach dieser A suspension of 21.3 g of H- (2-methoxy-6-methylphenyl) -N · - (ß-chloräthy 1) urea in 250 ml of water is heated under reflux for 45 minutes while stirring vigorously. After this
Le A 10 278- - 4 - ' Le A 10 278- - 4 - '
009852/2190009852/2190
Zeit ist alles in Lösung gegangen. Man konzentriert im Vakuum auf ca. 125 ml, filtriert von minimalen Verunreinigungen ab und versetzt das Filtrat mit Ammoniak. Das ausgefallene 2-(2-Methoxy-6-methylplienylamino)-2-oxazolin wird aus Benzol umgelöst. F. 119 bis 12O0C. Ausbeute 13,8 g.Time everything went into solution. It is concentrated in vacuo to approx. 125 ml, minimal impurities are filtered off and ammonia is added to the filtrate. The precipitated 2- (2-methoxy-6-methylplienylamino) -2-oxazoline is redissolved from benzene. F. 119 g to 12O 0 C. Yield 13.8.
Der als Ausgangsmaterial verwendete N-(2-Methoxy-6-methylphenyl)-N'-(ß-chloräthyl)-harnstoff, P. 1560C, wird durch Umsetzung von 2-Methoxy-6-methylanilin mit ß-Chloräthylisocyanat erhalten.The N- (2-methoxy-6-methylphenyl) -N '- (β-chloroethyl) urea, P. 156 0 C, used as the starting material is obtained by reacting 2-methoxy-6-methylaniline with β-chloroethyl isocyanate.
Zu einer lösung von 1-6,35 g Natriumhydroxid in 160 ml Wasser gibt man 16,35 g 9O-$iges Äthanolamin und tropft eine Lösung von 43,6 g ^-Methoxy-o-methylphenylisocyaniddichlorid in 50 ml Bioxan ein. Die Temperatur steigt dabei auf 50 bis 6O0C. Man rührt noch 1 Stunde bei 500C, kühlt ab und saugt vom ausgeschiedenen 2-(2-Methoxy-6~methylphenylamino)-2-oxazolin ab. F. 119 bis 12O0C. Ausbeute 35 g»16.35 g of 9O- $ iges ethanolamine are added to a solution of 1-6.35 g of sodium hydroxide in 160 ml of water and a solution of 43.6 g of ^ -methoxy-o-methylphenyl isocyanide dichloride in 50 ml of bioxane is added dropwise. The temperature rises to 50 to 6O 0 C. Stirring is continued for 1 hour at 50 0 C, cooled and sucks from the precipitated 2- (2-methoxy-6 ~ methylphenylamino) -2-oxazoline from. F. 119 to 12O 0 C. Yield 35 g »
Das Ausgangsmaterial wird auf folgendem Wege erhalten: N-Formyl-2-methoxy-6-methylanilin wird mit Phosgen in Gegenwart von Triäthylamin in 2-Methoxy-6-methylphenylisonitril, * KPq . 70 bis 740C, übergeführt. Nachfolgende Anlagerung von Chlor bei 0 bis 50C in Chloroformlösung liefert das 2-Methoxy-6-phenylisocyaniddichlorid vo KpQ . 84 bis 860C.The starting material is obtained in the following way: N-formyl-2-methoxy-6-methylaniline is treated with phosgene in the presence of triethylamine in 2-methoxy-6-methylphenylisonitrile, * KPq . 70 to 74 0 C, transferred. Subsequent addition of chlorine at 0 to 5 ° C. in chloroform solution gives the 2-methoxy-6-phenyl isocyanide dichloride of bp Q. 84 to 86 0 C.
Nach der in Beispiel 1 beschriebenen Methode erhält man durch Cyclisierung von EK2.6-Dimethoxyphenylamino)-N!-ßchioräthy!harnstoff, F. 172 bis 1730C, das 2-(2.6-Di-According to the method described in Example 1, cyclization of EK2.6-dimethoxyphenylamino) -N ! -ßchioräthy! urea, F. 172 to 173 0 C, the 2- (2.6-Di-
Le A 10 278 -* 5 -Le A 10 278 - * 5 -
009852/219Q009852 / 219Q
methoxyphenylamino)-2-oxazolin, F. 168 bis 1690C (aus Alkohol). Ausbeute 83 ^.methoxyphenylamino) -2-oxazoline, m.p. 168 to 169 0 C (from alcohol). Yield 83 ^.
Üe A 10 278 - 6 - Üe A 10 278 - 6 -
009852/2190009852/2190
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0050294 | 1966-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1670752A1 true DE1670752A1 (en) | 1970-12-23 |
Family
ID=7103684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661670752 Pending DE1670752A1 (en) | 1966-09-27 | 1966-09-27 | Process for the preparation of 2-phenylamino-oxazolines |
Country Status (5)
| Country | Link |
|---|---|
| AT (2) | AT273104B (en) |
| BE (1) | BE704393A (en) |
| DE (1) | DE1670752A1 (en) |
| FR (1) | FR1557684A (en) |
| GB (1) | GB1138530A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2362754A1 (en) * | 1972-12-28 | 1974-07-11 | Science Union & Cie | CYCLOPROPYLMETHYLAMINES, THE PROCESS FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| DE2951247A1 (en) * | 1978-12-20 | 1980-07-03 | Science Union & Cie | N-SUBSTITUTED TRIFLUORAETHYLAMINE, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING IT |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH623044A5 (en) * | 1974-12-02 | 1981-05-15 | Scherico Ltd | Process for the preparation of novel anilino-2-oxazolines |
| JPS52111541A (en) * | 1976-02-19 | 1977-09-19 | Scherico Ltd | Substituted ureido compound and medical composition containing it as active ingredient |
| US4256755A (en) | 1980-04-28 | 1981-03-17 | E. I. Du Pont De Nemours & Company | Method of using N-substituted dihydro-2-oxazolamines as analgesics |
-
1966
- 1966-09-27 DE DE19661670752 patent/DE1670752A1/en active Pending
-
1967
- 1967-09-21 AT AT860367A patent/AT273104B/en active
- 1967-09-21 AT AT814468A patent/AT273107B/en active
- 1967-09-27 GB GB4399867A patent/GB1138530A/en not_active Expired
- 1967-09-27 BE BE704393D patent/BE704393A/xx unknown
- 1967-09-27 FR FR1557684D patent/FR1557684A/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2362754A1 (en) * | 1972-12-28 | 1974-07-11 | Science Union & Cie | CYCLOPROPYLMETHYLAMINES, THE PROCESS FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| DE2951247A1 (en) * | 1978-12-20 | 1980-07-03 | Science Union & Cie | N-SUBSTITUTED TRIFLUORAETHYLAMINE, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING IT |
Also Published As
| Publication number | Publication date |
|---|---|
| AT273104B (en) | 1969-08-11 |
| BE704393A (en) | 1968-03-27 |
| FR1557684A (en) | 1969-02-21 |
| GB1138530A (en) | 1969-01-01 |
| AT273107B (en) | 1969-08-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69017479T2 (en) | Azabicyclohepten derivatives and their salts, processes for their preparation, their use as medicaments and preparations containing them. | |
| DE1670752A1 (en) | Process for the preparation of 2-phenylamino-oxazolines | |
| DE2454107A1 (en) | SUBSTITUTED UREA, ACYLURA AND SULFONYLURA DERIVATIVES AND PROCESS FOR THEIR PRODUCTION | |
| DE2308305A1 (en) | PROCESS FOR THE PREPARATION OF 4-HYDROXY-3- (5-METHYL-3-ISOXAZOLYLCARBAMOYL) 2-METHYL-2H-1,2-BENZOTHIAZINE-1,1-DIOXIDE | |
| DE1670751A1 (en) | Process for the preparation of 2-phenylamino-2-oxazolines | |
| DE1917739A1 (en) | New derivatives of thiocarbamic acid | |
| DE1545666A1 (en) | New diazacyloalkane compounds | |
| DE2035797A1 (en) | New nitrofurandenvates, a process for their production and their use as pharmaceuticals | |
| DE1670755A1 (en) | Process for the preparation of 2-phenylamino-2-oxazolines | |
| DE2443297A1 (en) | ANTHELMINTHICALLY ACTIVE BASIC SUBSTITUTED 2-CARBALKOXY-AMINO-BENZIMIDAZOLYL-5 (6) -PHENYL ETHERS AND KETONES AND THE PROCESS FOR THEIR PRODUCTION | |
| DE1670754A1 (en) | Process for the preparation of 2-phenylimino-oxazolidines | |
| DE2250469A1 (en) | PROCESS FOR THE PREPARATION OF SUBSTITUTED BENZIMIDAZOLES | |
| DE1620054C (en) | Process for the preparation of quinolindenvates and drugs containing these compounds excretion from 1470047 | |
| DE2409387A1 (en) | PROCESS FOR THE PREPARATION OF 2,5 DISUBSTITUTED BENZAMIDES | |
| DE1470070C (en) | Process for the preparation of benzimidazole derivatives | |
| DE1593783A1 (en) | Process for the preparation of 1- (2-nitrilophenoxy) -2-hydroxy-3-isopropylaminopropane and its salts | |
| DE1470047C (en) | Chinohndenvate and a process for their preparation | |
| DE1670943A1 (en) | Process for the manufacture of parabean acid derivatives | |
| AT236950B (en) | Process for the production of new triazolidines | |
| DE2253554A1 (en) | 2-AMINO-2-OXAZOLINE AND THE PROCESS FOR THEIR PRODUCTION | |
| DE2327414A1 (en) | PROCESS FOR THE PREPARATION OF 2-ALKOXY-4,5-SUBSTITUTED BENZAMIDES | |
| DE1670378C (en) | Process for the preparation of the salt from 4-n-butyl-3,5-dioxo-1,2-diphenylpyrazolidine and the beta-diethylamino-ethylamide of p-chlorophenoxyacetic acid | |
| DE1445722C (en) | Carboxylic acid epiperazides | |
| DE2408171C3 (en) | Silyl oxazolidinone compounds and processes for their preparation | |
| DE1670383A1 (en) | Novel tetrahydroimidazoles and processes for their preparation |