DE1226563B - Process for the preparation of carbonyl compounds - Google Patents

Process for the preparation of carbonyl compounds

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Publication number
DE1226563B
DE1226563B DEB79139A DEB0079139A DE1226563B DE 1226563 B DE1226563 B DE 1226563B DE B79139 A DEB79139 A DE B79139A DE B0079139 A DEB0079139 A DE B0079139A DE 1226563 B DE1226563 B DE 1226563B
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Germany
Prior art keywords
denotes
general formula
radical
carbonyl compounds
nitrile
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
Application number
DEB79139A
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German (de)
Inventor
Dr Horst Koenig
Dr Horst Metzger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to DEB87722A priority Critical patent/DE1239288B/en
Priority to DEB79140A priority patent/DE1238454B/en
Priority to DEB79139A priority patent/DE1226563B/en
Priority to DEB79138A priority patent/DE1226562B/en
Priority to CH1445765A priority patent/CH468970A/en
Priority to FR36755A priority patent/FR1461695A/en
Priority to BE671693D priority patent/BE671693A/xx
Priority to NL6514088A priority patent/NL6514088A/xx
Priority to GB45818/65A priority patent/GB1120737A/en
Publication of DE1226563B publication Critical patent/DE1226563B/en
Priority to US00863770A priority patent/US3821277A/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/14—Preparation of nitro compounds by formation of nitro groups together with reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C205/51—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C247/12—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
    • C07C331/02—Thiocyanates
    • C07C331/14—Thiocyanates having sulfur atoms of thiocyanate groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • 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
    • C07D213/24—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 with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

BUNDESREPUBLIK DEUTSCHLANDFEDERAL REPUBLIC OF GERMANY

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

AUSLEGESCHRIFTEDITORIAL

Int. Cl.: Int. Cl .:

Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:

C07cC07c

C07dC07d

Deutsche Kl.: 12 ο -16German class: 12 ο -16

1226563 B79139IVb/12o 30. Oktober 1964 13. Oktober 19661226563 B79139IVb / 12o October 30, 1964 October 13, 1966

Es wurde gefunden, daß man Carbonylverbindungen der allgemeinen FormelIt has been found that carbonyl compounds of the general formula

O
R4 O
R 4

R2 RsR 2 Rs

CH — CH — CNCH - CH - CN

CH- CH- CNCH-CH-CN

I II I

R2 R3 R 2 R 3

IlIl

R1-C-CHR 1 -C-CH

IIII

H3CH 3 C

S = OS = O

CH3 CH 3

in der Ri die vorstehend genannte Bedeutung hat, Oin which Ri has the meaning given above, O

Verfahren zur Herstellung von
CarbonylverbindungenProcess for the production of
Carbonyl compounds

in der Ri einen Alkyl-, Aralkyl-, einen aromatischen oder heterocyclischen Rest oder den Rest — NHR5 bedeutet, worin R5 einen aliphatischen, araliphatischen, aromatischen oder heterocyclischen Rest bedeutet, Ra und R3 Wasserstoffatome oder die Methylgruppe bezeichnen und R2 außerdem die Nitrilgruppe sein kann und R4 einen niedermolekularen Alkylrest bedeutet, erhält, wenn man 1 Mol eines Dimethyloxosulfurylens der allgemeinen Formel Anmelder:in which Ri is an alkyl, aralkyl, aromatic or heterocyclic radical or the radical - NHR5, where R5 is an aliphatic, araliphatic, aromatic or heterocyclic radical, Ra and R3 denote hydrogen atoms or the methyl group and R 2 is also the nitrile group can and R4 is a low molecular weight alkyl radical is obtained if 1 mol of a dimethyloxosulfurylene of the general formula Applicant:

Badische Anilin- & Soda-FabrikAniline & Soda Factory in Baden

Aktiengesellschaft, Ludwigshafen/RheinAktiengesellschaft, Ludwigshafen / Rhein

Als Erfinder benannt:Named as inventor:

Dr. Horst König,Dr. Horst König,

Dr. Horst Metzger, Ludwigshafen/RheinDr. Horst Metzger, Ludwigshafen / Rhine

mit wenigstens 2 Mol eines ungesättigten Nitrils der allgemeinen Formelwith at least 2 moles of an unsaturated nitrile of the general formula

CH = C — CN
R2 R3 CH = C - CN
R 2 R 3

worin R2 und R3 die vorstehend genannte Bedeutung haben, und einem niedermolekularen Alkanol der Formel R4OH, worin R4 die vorstehend genannte Bedeutung hat, bei Temperaturen zwischen 0 und 70°C, gegebenenfalls in Gegenwart eines organischen Lösungsmittels, umsetzt.in which R 2 and R3 have the meaning given above, and a low molecular weight alkanol of the formula R4OH, in which R4 has the meaning given above, is reacted at temperatures between 0 and 70 ° C., optionally in the presence of an organic solvent.

Das Verfahren läßt sich z. B. für die Umsetzung von Dimethyloxosulfurylenacetanilid mit Acrylsäurenitril in Gegenwart von Methanol durch folgendes Reaktionsschema wiedergeben:The method can be z. B. for the implementation of dimethyloxosulfurylenacetanilide with acrylonitrile in the presence of methanol represented by the following reaction scheme:

C6H5-NH-C-CH + 2CH2 = CH-CN + CH3OHC 6 H 5 -NH-C-CH + 2CH 2 = CH-CN + CH 3 OH

IlIl

ς — πς - π

H3C CH3 H 3 C CH 3

Il /CH2 — CH2 — CNII / CH 2 - CH 2 - CN

> C6H5NH -C-C^ + CH3S — CH3 > C 6 H 5 NH -CC ^ + CH 3 S - CH 3

I ^CH2-CH2-CN IlI ^ CH 2 -CH 2 -CN II

O OO O

CH3 CH 3

Die als Ausgangsstoffe der Fonnel II verwendeten 50 1 Mol eines Isocyanates, Ketens, Carbonsäure-Dimethyloxosulfurylene lassen sich z. B. durch Um- halogenide oder Carbonsäureanhydrids herstellen Setzung von 1 Mol Dimethyloxosulfoniumylid mit (vgl. die deutsche Auslegeschrift 1 207 379). Für dieThe 50 1 mol of an isocyanate, ketene, carboxylic acid dimethyloxosulfurylene used as starting materials of formula II can be z. B. produce halogenides or carboxylic acid anhydrides by adding 1 mole of dimethyloxosulfonium ylide (cf. German Auslegeschrift 1 207 379). For the

•609 670/428• 609 670/428

Umsetzung nach dem Verfahren der Erfindung ist es nicht unbedingt erforderlich, die Dimethyloxosulfurylene der Formel II aus deren Herstellungsgemisch abzutrennen. Als Ausgangsstoffe kann man z. B. Dimethyloxosulfurylenacetanilid, Dimethyloxosulfurylenacettoluidid, Dimethyloxosulfurylenessigsäuremethylamid, Dimethyloxosulfurylenaceton, Dimethyloxosulfurylenacetophenon und Dimethyloxosulfurylen-N-phenyläthylacetamid verwenden.Implementation according to the process of the invention, it is not absolutely necessary to use the dimethyloxosulfurylenes of the formula II to be separated from their preparation mixture. As starting materials you can z. B. Dimethyloxosulfurylenacetanilid, Dimethyloxosulfurylenacettoluidid, Dimethyloxosulfurylenessigsäuremethylamid, Dimethyloxosulfurylenaceton, Dimethyloxosulfurylenacetophenon and dimethyloxosulfurylene-N-phenylethylacetamide use.

Als ungesättigte Nitrile kann man z. B. Acrylsäurenitril, Methacrylsäurenitril, Crotonsäurenitril, Maleinsäure- oder Fumarsäurenitril verwenden.As unsaturated nitriles you can, for. B. Acrylic acid nitrile, methacrylic acid nitrile, crotonic acid nitrile, maleic acid or use fumaric acid nitrile.

Unter niedermolekularen Alkanolen der Formel R4OH sind solche zu verstehen, deren Rest R4 1 bis 8 Kohlenstoffatome enthält. Bevorzugt verwendet man unverzweigte Alkanole.Low molecular weight alkanols of the formula R 4 OH are to be understood in which the radical R contains from 4 1 to 8 carbon atoms. Unbranched alkanols are preferably used.

Das Verfahren läßt sich ohne Lösungsmittel durchführen. Man kann aber auch in Gegenwart von Lösungsmitteln arbeiten. Als Lösungsmittel eignen sich Kohlenwasserstoffe, wie Hexan, Heptan, Cyclohexan oder Benzol, ferner Äther, wie Diäthyläther oder Dibutyläther, N,N-disubstituierte Carbonsäureamide, wie Dimethylformamid oder N-Methylpyrrolidon. Schließlich kann man auch in Gegenwart von überschüssigem Alkohol arbeiten. Der Alkohol ist dabei gleichzeitig Reaktionsteilnehmer und Lösungsmittel. The process can be carried out without a solvent. But you can also do it in the presence of Solvents work. Hydrocarbons such as hexane, heptane and cyclohexane are suitable solvents or benzene, also ethers, such as diethyl ether or dibutyl ether, N, N-disubstituted carboxamides, such as dimethylformamide or N-methylpyrrolidone. After all, you can also do it in the present work from excess alcohol. The alcohol is both a reactant and a solvent.

1 Mol Dimethyloxosulfurylen reagiert mit 2 Mol Nitril und l'Molcdes Alkanols. Es ist jedoch zweckmäßig, das Nitril und das Alkanol in einem überschuß anzuwenden, z. B. je Mol Dimethyloxosulfurylen 3 bis 20 Mol Nitril und 10 bis 100 Mol Alkanole. Zur Abtrennung der gewünschten Verfahrensprodukte kann man die leicht flüchtigen Bestandteile aus dem Umsetzungsgemisch abdestillieren und den Rückstand Umkristallisieren.1 mole of dimethyloxosulfurylene reacts with 2 moles of nitrile and l'Molcdes alkanol. However, it is useful to apply the nitrile and the alkanol in excess, e.g. B. per mole of dimethyloxosulfurylene 3 to 20 moles of nitrile and 10 to 100 moles of alkanols. For the separation of the desired process products the volatile constituents can be distilled off from the reaction mixture and the residue Recrystallize.

Die nach dem Verfahren der Erfindung herstellbaren Verbindungen sind wertvolle Ausgangsstoffe für die Herstellung von Arzneimitteln und Pflanzenschutzmitteln. Außerdem können die Dinitrile zu bifunktionellen Säuren oder Aminen umgewandelt werden, die sich zu Kunststoffen verarbeiten lassen.The compounds which can be prepared by the process of the invention are valuable starting materials for the manufacture of pharmaceuticals and pesticides. In addition, the dinitrile can too bifunctional acids or amines, which can be processed into plastics.

Die in dem Beispiel angeführten Teile bedeuten Gewichtsteile,The parts given in the example mean parts by weight,

Beispielexample

4,22 Teile Dimethyloxosulfurylenacetanilid, 40 Teile frisch destilliertes Acrylsäurenitril und 40 Teile Methanol werden 45 Minuten unter Rückfluß erhitzt. Die leicht flüchtigen Bestandteile werden abdestilliert. Der Rückstand wird in 200 Teilen Benzol aufgenommen. Man wäscht mit 300 Teilen Wasser in drei Portionen, engt den Benzolextrakt ein und löst aus Cyclohexan und Essigester um. Man erhält 2,02 Teile kristallines y-Methoxy-y-carbanilido-a, ω-dicyanopentan vom F. = 820C, Die Ausbeute beträgt 40% der Theorie, bezogen auf angewandtes Dimethyloxosulfuryjenacetanilid. 4.22 parts of dimethyloxosulfurylene acetanilide, 40 parts of freshly distilled acrylonitrile and 40 parts of methanol are refluxed for 45 minutes. The volatile constituents are distilled off. The residue is taken up in 200 parts of benzene. It is washed with 300 parts of water in three portions, the benzene extract is concentrated and dissolved in cyclohexane and ethyl acetate. This gives 2.02 parts of crystalline y-methoxy-y-carbanilido-a, ω-dicyanopentane, mp = 82 0 C, The yield is 40% of theory, based on applied Dimethyloxosulfuryjenacetanilid.

Analyse: Ci5Hi7N3O2 (271,3).Analysis: Ci 5 Hi 7 N 3 O 2 (271.3).

Berechnet ... C 66,5, H 6,5, N 15,5, O 11,8%;
gefunden ... C 66,5, H 6,3, N 15,2, O 12,3%,Calculated ... C 66.5, H 6.5, N 15.5, O 11.8%;
found ... C 66.5, H 6.3, N 15.2, O 12.3%,

Claims (1)

Patentanspruch:Claim: Verfahren zur Herstellung von Carbonylverbindungen der allgemeinen FormelProcess for the preparation of carbonyl compounds of the general formula Ri — C — C<Ri - C - C < O
R4 O
R 4 R2 R3R2 R3 CH — CH — CNCH - CH - CN CH — CH — CN
R2 RsCH - CH - CN
R 2 Rs in der Ri einen Alkyl-, Aralkyl-, einen aromatischen oder heterocyclischen Rest oder den Rest —NHR5 bedeutet, worin R5 einen aliphatischen, araliphatischen, aromatischen oder heterocyclischen Rest bedeutet, R2 und R3 Wasserstoffatome oder die Methylgruppe bezeichnen und R2 außerdem die Nitrilgruppe sein kann und R4 einen niedermolekularen Alkylrest bedeutet, dadurch gekennzeichnet, daß man 1 Mol eines Dimethyloxosulfurylens der allgemeinen Formelin which Ri denotes an alkyl, aralkyl, an aromatic or heterocyclic radical or the radical —NHR5, in which R5 denotes an aliphatic, araliphatic, aromatic or heterocyclic radical, R 2 and R3 denote hydrogen atoms or the methyl group and R 2 also denotes the nitrile group can be and R4 denotes a low molecular weight alkyl radical, characterized in that 1 mol of a dimethyloxosulfurylene of the general formula Ri — C — CHRi - C - CH H3CH 3 C CH3 CH 3 in der Ri die vorstehendgenannte Bedeutung hat, mit wenigstens 2 Mol eines ungesättigten Nitrils der allgemeinen Formelin which Ri has the above meaning, with at least 2 moles of an unsaturated nitrile of the general formula CH = C — CN
R2 R3 CH = C - CN
R 2 R 3 in der R2 und R3 die vorstehend genannte Bedeutung haben, und einem niedermolekularen Alkanol der Formel R4OH, worin R4 die vorstehend genannte Bedeutung hat, bei Temperaturen zwischen 0 und 700C, gegebenenfalls in Gegenwart eines organischen Lösungsmittels, umsetzt.have in the R 2 and R 3 are each as defined above, and a low molecular weight alkanol of the formula R 4 OH wherein R 4 has the abovementioned meaning, at temperatures between 0 and 70 0 C, optionally in the presence of an organic solvent, are reacted.
DEB79139A 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds Pending DE1226563B (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DEB87722A DE1239288B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
DEB79140A DE1238454B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
DEB79139A DE1226563B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
DEB79138A DE1226562B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
CH1445765A CH468970A (en) 1964-10-30 1965-10-20 Process for the preparation of carbonyl compounds substituted in a-position
FR36755A FR1461695A (en) 1964-10-30 1965-10-29 Process for the production of alpha-substituted carbonyl compounds
BE671693D BE671693A (en) 1964-10-30 1965-10-29
NL6514088A NL6514088A (en) 1964-10-30 1965-10-29
GB45818/65A GB1120737A (en) 1964-10-30 1965-10-29 Production of carbonyl compounds substituted in ª‡-position
US00863770A US3821277A (en) 1964-10-30 1969-10-02 Ypsilon-methoxy-ypsilon-carbanilino-alpha,omega-dicyanopentane

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DEB87722A DE1239288B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
DEB79140A DE1238454B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
DEB79139A DE1226563B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
DEB79138A DE1226562B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds

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DE1226563B true DE1226563B (en) 1966-10-13

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DEB79139A Pending DE1226563B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
DEB79140A Pending DE1238454B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
DEB79138A Pending DE1226562B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
DEB87722A Pending DE1239288B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds

Family Applications After (3)

Application Number Title Priority Date Filing Date
DEB79140A Pending DE1238454B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
DEB79138A Pending DE1226562B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds
DEB87722A Pending DE1239288B (en) 1964-10-30 1964-10-30 Process for the preparation of carbonyl compounds

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BE (1) BE671693A (en)
CH (1) CH468970A (en)
DE (4) DE1226563B (en)
GB (1) GB1120737A (en)
NL (1) NL6514088A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3313917A1 (en) * 1983-04-16 1984-10-25 Basf Ag, 6700 Ludwigshafen METHOD FOR PRODUCING VICINAL POLYCARBONYL COMPOUNDS
CN115557865B (en) * 2022-10-17 2024-05-14 南京工业大学 Thioether-promoted cysteine-based bioconjugate method

Also Published As

Publication number Publication date
NL6514088A (en) 1966-05-02
DE1226562B (en) 1966-10-13
GB1120737A (en) 1968-07-24
DE1239288B (en) 1967-04-27
DE1238454B (en) 1967-04-13
CH468970A (en) 1969-02-28
BE671693A (en) 1966-04-29

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