DE1204663B - Process for the preparation of N-o-cyano-phenyl-N ', N'-dialkylformamidinium salts - Google Patents
Process for the preparation of N-o-cyano-phenyl-N ', N'-dialkylformamidinium saltsInfo
- Publication number
- DE1204663B DE1204663B DEB77076A DEB0077076A DE1204663B DE 1204663 B DE1204663 B DE 1204663B DE B77076 A DEB77076 A DE B77076A DE B0077076 A DEB0077076 A DE B0077076A DE 1204663 B DE1204663 B DE 1204663B
- Authority
- DE
- Germany
- Prior art keywords
- formula
- parts
- chloride
- oxime
- isatin
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Description
BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY
DEUTSCHESGERMAN
PATENTAMTPATENT OFFICE
AUSLEGESCHRIFTEDITORIAL
Int. Cl.:Int. Cl .:
Deutsche Kl.:German class:
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
C07cC07c
C07d
12O-22C07d
12O-22
B77076IVb/12o
4.Juni 1964
11. November 1965B77076IVb / 12o
June 4, 1964
November 11, 1965
Es ist bekannt, daß man durch Umsetzung von Amidchloriden mit primären Aminen Ν,Ν',Ν'-ίΓί-substituierte Amidiniumsalze erhält. Diese Arbeitsweise kann man auch für die Herstellung von N-o-Cyänöphenyl-N^N'-dialkylformamidiniumchloriden aus o-Aminobenzonitril und Ν,Ν'-Dialkylformamidchloriden anwenden. Ein großer Nachteil dieses Verfahrens besteht jedoch darin, daß o-Aminobenzonitril und insbesondere substituierte o-Aminobenzonitrile nur sehr schwer zugängliche Stoffe sind.It is known that Ν, Ν ', Ν'-ίΓί-substituted by reacting amide chlorides with primary amines Amidinium salts obtained. This procedure can also be used for the preparation of N-o-Cyänophenyl-N ^ N'-dialkylformamidinium chlorides from o-aminobenzonitrile and Ν, Ν'-dialkylformamide chlorides use. A major disadvantage of this process, however, is that o-aminobenzonitrile and in particular substituted o-aminobenzonitriles are very difficult to access substances.
Es wurde nun gefunden, daß man N-o-Cyanophenyl-N',N'-dialkylformamidiniumsalze der allgemeinen FormelIt has now been found that N-o-cyanophenyl-N ', N'-dialkylformamidinium salts the general formula
= CH_ = CH _
R1
R2 R 1
R 2
worin Ri und R2 gleiche oder verschiedene Alkylgruppen, R3 und R4 Wasserstoff, Halogen, Alkyl-, Alkoxy- oder Nitrogruppen bedeuten und Ri und R2 zusammen mit dem Stickstoffatom Glieder eines Ringes sein können, auf sehr einfache Weise aus leichter zugänglichen Ausgangsstoffen erhält, wenn man Isatin-ß-oxime der allgemeinen Formelwhere Ri and R2 are identical or different alkyl groups, R3 and R4 denote hydrogen, halogen, alkyl, alkoxy or nitro groups, and Ri and R2 together with the nitrogen atom can be members of a ring in a very simple way More readily available starting materials are obtained if isatin-ß-oxime of the general formula
NOHNOH
R3 R 3
IIII
worin R3 und R4 die zuvorgenannte Bedeutung haben, mit einem Ν,Ν-Dialkylformamidchlrid der allge-wherein R3 and R4 have the aforementioned meaning, with a Ν, Ν-dialkylformamide chloride of the general
NOHNOH
Rxx
R2'Rx x
R 2 '
N —CHClN -CHCl
Die als Ausgangsstoffe verwendeten Isatin-jS-oxime können im Benzolkern einen oder zwei Substituenten tragen. Die Substituenten R3 und R4 in der Formel II können Halogenatome, insbesondere Chlor oder Brom, Alfcylgruppen mit insbesondere 1 bis 4 Kohlenstoffatomen, Alkoxygruppen mit insbesondere 1 bis 4 Kohlenstoffatomen oder Nitrogruppen bedeuten. Sie können gleich oder verschieden sein. So sind Verfahren zur Herstellung von N-o-Cyanophenyl-N'jN'-dialkylformamidimumsalzen The isatin-jS-oxime used as starting materials can carry one or two substituents in the benzene nucleus. The substituents R3 and R4 in formula II halogen atoms, in particular chlorine or bromine, alfcyl groups with in particular 1 to 4 carbon atoms, Denote alkoxy groups with in particular 1 to 4 carbon atoms or nitro groups. They can be the same or different. So are processes for the preparation of N-o-cyanophenyl-N'jN'-dialkylformamidimum salts
Anmelder:Applicant:
Badische Anilin- & Soda-FabrikAniline & Soda Factory in Baden
Aktiengesellschaft,Corporation,
Ludwigshafen/RheinLudwigshafen / Rhine
Als Erfinder benannt:Named as inventor:
Dr. Matthias Seefelder,Dr. Matthias Seefelder,
Ludwigshafen/Rhein-GartenstadtLudwigshafen / Rhine garden city
meinen Formelmy formula
Rtx
R2'Rt x
R 2 '
N-CHClN-CHCl
Cl-Cl-
worin Ri und R2 die zuvorgenannte Bedeutung haben, oder mit einem Umsetzungsprodukt eines N,N-Dialkylformamids der Formelwherein Ri and R 2 have the aforementioned meaning, or with a reaction product of an N, N-dialkylformamide of the formula
Rr
R2 Rr
R 2
N-CHON-CHO
worin Ri und R2 die zuvorgenannte Bedeutung haben, mit Phosphoroxychlorid, Phosphortrjchlorid, Phosphorpentachlorid oder Sulfurylchlorid bei Temperaturen zwischen 0 und 100° C in Gegenwart eines inerten Lösungsmittels umsetzt.where Ri and R 2 have the aforementioned meaning, reacted with phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride or sulfuryl chloride at temperatures between 0 and 100 ° C. in the presence of an inert solvent.
Das Verfahren läßt sich durch folgende Reaktionsgleichung wiedergeben:The process can be represented by the following reaction equation:
R3 R 3
* (
R4 * (
R 4
CNCN
N = CH-NN = CH-N
Ri ■ HClRi ■ HCl
R2 + CO2 + HClR 2 + CO 2 + HCl
ζ. B. Isatinoxim, 5-Nitro-isatinoxim, 5,7-Dibromisatinoxim, 5-Chlor-isatinoxim oder 5-Methyl-isatinoxim der Reaktion zugänglich. Sie lassen sich leicht z. B. durch Umsetzung der entsprechenden Isatine mit Hydroxylamin herstellen.ζ. B. isatin oxime, 5-nitro-isatin oxime, 5,7-dibromoisatin oxime, 5-chloro-isatin oxime or 5-methyl-isatin oxime accessible to the reaction. You can easily z. B. by implementing the corresponding isatins make with hydroxylamine.
Als Ν,Ν-Dialkylformamidchloride der Formel II verwendet man vorzugsweise solche, in denen die Reste Ri und R2 niedere Alkylgruppen mit z. B.As Ν, Ν-dialkylformamide chlorides of the formula II are preferably used in which the radicals Ri and R 2 are lower alkyl groups with z. B.
509 737/402509 737/402
1 bis 4 Kohlenstoffatomen bedeuten. Die Alkylgruppen können auch zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen gesättigten, vorzugsweise fünf- oder sechsgliedrigen Ring bilden. So kann man z. B. Ν,Ν-Dimethylfomamidchlorid, Ν,Ν-Dibutylformamidchlorid, N-Methyl-N-äthylformamidchlorid, die Amidchloride des Formylpyrrolidins, Formylpiperidins oder Formylmorpholins verwenden. Die Formamidchloride lassen sich sehr einfach durch Umsetzung des entsprechenden ι ο Formamide mit Phosgen, Oxalylchlorid oder Thionylchlorid herstellen. An Stelle der Amidchloride kann man auch die Umsetzungsprodukte der entsprechenden N,N-disubstituierten Formamide mit Phosphoroxychlorid, Phosphortrichlorid, Phosphorpentachlorid oder Sulfurylchlorid verwenden, die unter den Reaktionsbedingungen wie Formamidchloride reagieren.Mean 1 to 4 carbon atoms. The alkyl groups can also, together with the nitrogen atom to which they are bound, form a saturated, preferably form a five- or six-membered ring. So you can z. B. Ν, Ν-dimethylformamide chloride, Ν, Ν-dibutylformamide chloride, N-methyl-N-ethylformamide chloride, the amide chlorides of formylpyrrolidine, formylpiperidine or formylmorpholine use. The formamide chlorides can be very easily converted into the corresponding ι ο Make formamides with phosgene, oxalyl chloride or thionyl chloride. Instead of the amide chlorides, the reaction products of the corresponding N, N-disubstituted formamides with phosphorus oxychloride, Use phosphorus trichloride, phosphorus pentachloride or sulfuryl chloride, which are listed under react to the reaction conditions like formamide chlorides.
Solche Stoffe sind z. B. in HeIv. Chim. Acta, 42 (1959), S. 1653 und 1659, und inChem. Ber., 92 (1959), S. 837, beschrieben.Such substances are z. B. in HeIv. Chim. Acta, 42 (1959), pp. 1653 and 1659, and in Chem. Ber., 92 (1959), p. 837.
Das Verfahren wird vorzugsweise in Gegenwart inerter organischer Lösungsmittel durchgeführt. Solche Lösungsmittel sind z. B. Benzolkohlenwasserstoffe, wie Benzol, Toluol, Xylol, Äthylbenzol; Chlorkohlenwasserstoffe, wie Chloroform, Tetrachlorkohlenstoff, Tetrachlorätnan, Chlorbenzol, oder Äther wie Dibutyläther, Tetrahydrofuran, Dioxan. Man kann das Verfahren aber auch iri Gegenwart von Phosphoroxychlorid durchführen. ■The process is preferably carried out in the presence of inert organic solvents. Such solvents are e.g. B. benzene hydrocarbons such as benzene, toluene, xylene, ethylbenzene; Chlorinated hydrocarbons, such as chloroform, carbon tetrachloride, tetrachloroethane, chlorobenzene, or Ethers such as dibutyl ether, tetrahydrofuran, dioxane. The process can also be carried out in the presence perform of phosphorus oxychloride. ■
Man arbeitet bei Temperaturen zwischen 0 und 100°C. Bevorzugt wird bei Temperaturen zwischen 20 und 80° C gearbeitet.Temperatures between 0 and 100 ° C are used. Is preferred at temperatures between 20 and 80 ° C worked.
Zur Durchführung des Verfahrens kann man das Isatin-/J-oxim im Lösungsmittel gelöst vorlegen und das Formamidchlorid möglichst im gleichen Lösungsmittel gelöst oder suspendiert langsam zugeben. Man. kann die Reaktionsteilnehmer aber auch in umgekehrter Reihenfolge zueinander geben. In def Regel wendet man je Mol Isatin-jS-oxim 1 bis 1,1 Mol Amidchlorid an. Man kann jedoch auch mit einem größeren Überschuß des Amidchlorids, z. B. bis zum 5fachen Überschuß, arbeiten. Das Ende der Reaktion läßt sich leicht am Abklingen der Gasentwicklung feststellen. Man rührt zweckmäßigerweise nach der Beendigung der Gasentwicklung noch einige Zeit, z. B-. bis zu 3 Stunden, und kann dann nach dem Abkühlen und eventuellen Einengen das N-o- Cyanophenyl -Ν',Ν' - dialkylformamidiniumsalz leicht, z. B. durch Filtrieren oder Zentrifugieren, abtrennen.To carry out the process, the isatin- / J-oxime can be introduced in solution in the solvent and if possible, slowly add the formamide chloride dissolved or suspended in the same solvent. Man. but can also give the reaction participants in reverse order to each other. In def As a rule, 1 to 1.1 moles are used per mole of isatin-jS-oxime Amide chloride. However, you can also with a larger excess of the amide chloride, for. B. to to the 5-fold excess, work. The end of the reaction can easily be seen from the subsidence of the evolution of gas determine. It is advisable to stir after the evolution of gas has ceased some time, e.g. B-. up to 3 hours, and then can after cooling and possibly concentration, the N-o-cyanophenyl -Ν ', Ν' - dialkylformamidinium salt easy, e.g. B. by filtration or centrifugation, separate.
Aus den nach dem Verfahren hergestellten Stoffen lassen sich wertvolle Farbstoffe, Schädlingsbekämpfungsmittel und Pharmazeutika herstellen.Valuable dyes and pesticides can be converted from the substances produced by the process and manufacture pharmaceuticals.
Die in den Beispielen genannten Teile bedeuten Gewichtsteile.The parts mentioned in the examples are parts by weight.
In ein Gemisch von 130 Teilen Phosgen und 1000 Teilen Chloroform werden unter Kühlung 73 Teile Dimethylformamid langsam zugegeben. Man rührt 2 bis 3 Stunden nach und trägt dann bei Raumtemperatur 162 Teile Isatinoxim ein. Dabei setzt sofort Gasentwicklung ein. Wenn diese abklingt, wird auf Rückflußtemperatur erwärmt. Nach 2 bis 3 Stunden ist die Reaktion beendet. Nach dem Erkalten des Reaktionsgemisches wird abgesaugt und der Filterrückstand unter vermindertem Druck von anhaftendem Lösungsmittel befreit. Man erhält 130 Teile N-o - Cyanophenyl - Ν',Ν' - dimethylformamidinium-hydrochlorid vom F. 220 bis 222° C unter Zersetzung.In a mixture of 130 parts of phosgene and 1000 parts of chloroform, with cooling 73 parts of dimethylformamide were slowly added. The mixture is stirred for 2 to 3 hours and then contributes Room temperature 162 parts isatin oxime. Gas development starts immediately. When this subsides is heated to reflux temperature. The reaction has ended after 2 to 3 hours. After the reaction mixture has cooled, it is suctioned off and the filter residue is freed from adhering solvent under reduced pressure. You get 130 parts of N-o - cyanophenyl - Ν ', Ν' - dimethylformamidinium hydrochloride from 220 to 222 ° C with decomposition.
Zu einer Suspension von 128 Teilen N,N-Dimethylformamidchlorid in 1000 Teilen Toluol werden 208 Teile 5-Nitro-isatin-ß-oxim gegeben und 6 Stunden bei Raumtemperatur gerührt. Durch 2stündiges Erhitzen auf Rückflußtemperatur wird die Reaktion zu Ende gebracht. Nach dem Abkühlen lassen sich 245 Teile N-(2-Cyan-4-nitro)-phenyl-N',N'-dimethylformamidinium-hydrochlorid durch einfaches Absaugen isolieren, das bei 212 bis 213° C unter Zersetzung schmilzt.To a suspension of 128 parts of N, N-dimethylformamide chloride 208 parts of 5-nitro-isatin-ß-oxime are added to 1000 parts of toluene and 6 hours stirred at room temperature. The reaction is stopped by heating at reflux temperature for 2 hours brought to an end. After cooling, 245 parts of N- (2-cyano-4-nitro) -phenyl-N ', N'-dimethylformamidinium hydrochloride can be found isolate by simple suction, which melts at 212 to 213 ° C with decomposition.
In eine Lösung von 128 Teilen N,N-Dimethylformamidchlorid in 1000 Teilen Chloroform werden bei 50°C 320 Teile 5,7-Dibrom-isatin-ß-oxim langsam eingetragen, so daß die Gasentwicklung nicht zu stürmisch wird. Man rührt 2 Stunden bei 50° C nach, kühlt auf 0°C ab und isoliert das kristalline Produkt durch Absaugen. Nach kurzem Trocknen unter vermindertem Druck erhält man 320 Teile N-(2-Cyan-4,6-dibrom)-phenyl-N',N'-dimethylformamidinium-hydrochlorid mit einem- Schmelzpunkt von 215 bis 216°C unter Zersetzung.In a solution of 128 parts of N, N-dimethylformamide chloride in 1000 parts of chloroform, 320 parts of 5,7-dibromo-isatin-ß-oxime slowly become at 50 ° C entered so that the gas evolution does not become too stormy. The mixture is stirred at 50 ° C. for 2 hours after, cools to 0 ° C and isolates the crystalline product by suction. After a short drying time 320 parts of N- (2-cyano-4,6-dibromo) -phenyl-N ', N'-dimethylformamidinium hydrochloride are obtained under reduced pressure with a melting point of 215 to 216 ° C with decomposition.
Zu einer Lösung von 128 Teilen N,N-Dimethylformamidchlorid in 1000.Teilen Chloroform . gibt man bei Raumtemperatur 176 Teile 5-MethyUsatinß-oxim und rührt bei dieser Temperatur bis die Gasentwicklung beendet ist. Man saugt den ausgefallenen Niederschlag ab und trocknet kurz unter vermindertem Druck und· erhält 195 Teile N-(2-Cyan-5-methyl)-phenyl-N',N'-dimethylformamidinium - hydrochlorid mit einem Schmelzpunkt von 216 bis 218° C unter Zersetzung.To a solution of 128 parts of N, N-dimethylformamide chloride in 1000 parts of chloroform. gives one at room temperature 176 parts of 5-MethyUsatinß-oxime and stir at this temperature until the evolution of gas has ceased. One sucks the fancy Precipitate is removed and dried briefly under reduced pressure, giving 195 parts of N- (2-cyano-5-methyl) -phenyl-N ', N'-dimethylformamidinium - hydrochloride with a melting point of 216 to 218 ° C with decomposition.
Zu einer Lösung von 130 Teilen Phosgen in 1500 Teilen Chloroform gibt man langsam 100 Teile N-Formyl-pyrrolidin und rührt das Gemisch 3 Stunden bei Raumtemperatur. Danach werden 160 Teile Isatin-ß-oxim langsam eingetragen, so daß die Gasentwicklung nicht zu lebhaft wird. Anschließend wird 1 Stunde auf Rückflußtemperatur erwärmt. Nach dem Abkühlen werden durch Absaugen und Umkristallisieren des kristallinen Produkts aus Äthanol 120 Teile N-(o-Cyan)-phenyl-N',N'-tetramethylenformamidinium-hydrochlorid gewonnen, das bei 245 bis 247°C unter Zersetzung schmilzt.100 parts are slowly added to a solution of 130 parts of phosgene in 1500 parts of chloroform N-formyl-pyrrolidine and the mixture is stirred for 3 hours at room temperature. After that there are 160 parts Isatin-ß-oxime entered slowly, so that the evolution of gas doesn't get too lively. The mixture is then heated to reflux temperature for 1 hour. After cooling, the crystalline product is extracted by suction and recrystallization Ethanol 120 parts of N- (o-cyano) -phenyl-N ', N'-tetramethyleneformamidinium hydrochloride obtained, which melts at 245 to 247 ° C with decomposition.
Claims (1)
HeIv. Chim. Acta, 42 (1959), S. 1653, 1659;
Chem. Berichte, 92 (1959), S. 837.Considered publications:
HeIv. Chim. Acta, 42 (1959), pp. 1653, 1659;
Chem. Reports, 92 (1959), p. 837.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB77076A DE1204663B (en) | 1964-06-04 | 1964-06-04 | Process for the preparation of N-o-cyano-phenyl-N ', N'-dialkylformamidinium salts |
| CH695665A CH445474A (en) | 1964-06-04 | 1965-05-18 | Process for the preparation of N-o-cyanophenyl-N ', N'-dialkylformamidinium salts |
| FR19427A FR1435612A (en) | 1964-06-04 | 1965-06-03 | Process for the production of nu-o-cyanophenyl-nu ', nu'-dialkoylformamidinium salts |
| BE664907D BE664907A (en) | 1964-06-04 | 1965-06-03 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB77076A DE1204663B (en) | 1964-06-04 | 1964-06-04 | Process for the preparation of N-o-cyano-phenyl-N ', N'-dialkylformamidinium salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1204663B true DE1204663B (en) | 1965-11-11 |
Family
ID=6979320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB77076A Pending DE1204663B (en) | 1964-06-04 | 1964-06-04 | Process for the preparation of N-o-cyano-phenyl-N ', N'-dialkylformamidinium salts |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE664907A (en) |
| CH (1) | CH445474A (en) |
| DE (1) | DE1204663B (en) |
| FR (1) | FR1435612A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1245768B (en) | 1963-01-29 | 1967-07-27 | Eaton Yale & Towne | Floor conveyor vehicle with a brake arranged at the upper end of the drive unit |
-
1964
- 1964-06-04 DE DEB77076A patent/DE1204663B/en active Pending
-
1965
- 1965-05-18 CH CH695665A patent/CH445474A/en unknown
- 1965-06-03 FR FR19427A patent/FR1435612A/en not_active Expired
- 1965-06-03 BE BE664907D patent/BE664907A/fr unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1245768B (en) | 1963-01-29 | 1967-07-27 | Eaton Yale & Towne | Floor conveyor vehicle with a brake arranged at the upper end of the drive unit |
Also Published As
| Publication number | Publication date |
|---|---|
| BE664907A (en) | 1965-12-31 |
| FR1435612A (en) | 1966-04-15 |
| CH445474A (en) | 1967-10-31 |
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