IL42152A - The production of alpha-iminonitriles - Google Patents

The production of alpha-iminonitriles

Info

Publication number
IL42152A
IL42152A IL42152A IL4215273A IL42152A IL 42152 A IL42152 A IL 42152A IL 42152 A IL42152 A IL 42152A IL 4215273 A IL4215273 A IL 4215273A IL 42152 A IL42152 A IL 42152A
Authority
IL
Israel
Prior art keywords
process according
carbon atoms
alkyl
effected
variant
Prior art date
Application number
IL42152A
Other versions
IL42152A0 (en
Original Assignee
Bayer Ag
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 Bayer Ag filed Critical Bayer Ag
Publication of IL42152A0 publication Critical patent/IL42152A0/en
Publication of IL42152A publication Critical patent/IL42152A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members 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
    • C07D253/075—Two hetero atoms, in positions 3 and 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
    • C07D307/73—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by amino or imino, or substituted amino or imino radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Claims (16)

42152/2 CLAIMS , · .. . ' . . '
1. A process for the production of an a--imino-nitrile the general formula in which R and may be identical or different, are each an alkyl, alkenyl, cycloalkyl, aralkyl, aryl or · uranyl radical, which radical can be carrying one or more substituents selected from halogen, alkyl, cyano and nitro groups, 1 f " "! R alternatively being a / morpholino » | alkoxy or acyloxy radical, in which an imide halide of the general formula in which R and ^ have the above-mentioned meanings and X is halogen, preferably chlorine or bromine, is reacted either ' (a) with a metal cyanide of the general formula M(CN)n (III) in which M represents an n-valent metal cation, or Le A 14 286 - 25 - 42152/2 (b) with hydrogen cyanide or a compound which releases hydrogen cyanide, in the presence of an acid-binding agent.
2. A process according to Claim 1 , in which R is alkyl with 1-8 carbon atoms which may be substituted by halogen; alkeny1! with 2-8 carbon atoms; cycloalkyl with 3-8 carbon atoms ■ which may be substituted by alkyl with 1-3 carbon atoms; optionally substituted aryl with 6 to 10 carbon atoms; or an optionally substituted furanyl ring, substituents for the two last-mentioned radicals being selected from halogen, alkyl and nitro groups; and is alkyl with 1-7 carbon atoms; optionally substituted cycloalkyl with 5-8 carbon atoms; orpholinoj or optionally substituted aryl with 6-10 carbon atoms.
3. A process according to claim 1 or 2, in which the reaction is effected in the presence of an inert organic diluent.
4. A process according to claim 1, 2 or 3» in which the reaction is effected at from 0° to 180°C.
5. A process according to claim 4» in which the reaction is effected at from 20° to 140°C.
6. A process according to any of claims 1 to 5» in which the reaction is effected in the presence of a catalyst.
7. A process according to claim 6, in which the catalyst is a tertiary amine, in the case of variant (a), or a metal or metal salt, in the case of variant (b).
8. A process according to claim 7» in which the catalyst is pyridine, in the case of variant (a), or copper or a copper salt, in the case of variant (b). Le A 14 286 . - 26 -
9. A process according to claim 1(a), or any of claims 2 to 8 as appendant to claim 1(a), in which M is an alkali metal cation, an alkaline earth metal cation or a metal cation of group lb or . lib of the Periodic System.
10. A process according to claim 9» in which the metal cyanide is one that is hereinbefore specifically named.
11. A process according to claim 1(b), or any of claims 2 to 8 as appendant to claim.1(b), in which the acid-binding agent is a tertiary amine.
12. A process according to claim 1(b), any of claims 2 to 8 as appendant to claim 1(b), or claim 11, in which a cyano-hydrin is used, as a compound which releases hydrogen cyanide.
13. . A process according to claim 12, in which the cyanohydrin is one that is hereinbefore specifically named.
14. A process according to any of claims 1 to 13» in which the imid^ halide (II) is prepared from the corresponding acid amide by halogenation and is then reacted in situ.
15. A process for the production of a compound of the formula (I) in claim 1 , substantially as hereinbefore described in any of the Examples.
16. Compounds of the formula (I) in claim 1 whenever prepared by a process according to any of claims 1 to 15. Le A 14 286 - 27 -
IL42152A 1972-05-04 1973-05-01 The production of alpha-iminonitriles IL42152A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2221771A DE2221771C3 (en) 1972-05-04 1972-05-04 Process for the preparation of α-iminonitriles

Publications (2)

Publication Number Publication Date
IL42152A0 IL42152A0 (en) 1973-07-30
IL42152A true IL42152A (en) 1976-01-30

Family

ID=5844001

Family Applications (1)

Application Number Title Priority Date Filing Date
IL42152A IL42152A (en) 1972-05-04 1973-05-01 The production of alpha-iminonitriles

Country Status (9)

Country Link
JP (1) JPS4961120A (en)
BE (1) BE799032A (en)
CH (1) CH579030A5 (en)
DE (1) DE2221771C3 (en)
FR (1) FR2183259B1 (en)
GB (1) GB1374401A (en)
IL (1) IL42152A (en)
IT (1) IT986990B (en)
NL (1) NL7306266A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2471369A1 (en) * 1979-12-17 1981-06-19 Roussel Uclaf NOVEL IMINES, DERIVANT OF FORMYL CYCLOPROPANE CARBOXYLIC ACID ESTERS, PROCESS FOR THEIR PREPARATION AND THEIR USE IN THE PREPARATION OF INSECTICIDAL ESTERS
CA1224471A (en) * 1980-06-20 1987-07-21 Shell Canada Limited Phenylamino (imino) - acetonitrile plant growth regulating agents
US5182305A (en) * 1986-08-08 1993-01-26 Colgate-Palmolive Co. N-aryl and n-cycloakyl neoalkanamide insect repellents

Also Published As

Publication number Publication date
FR2183259A1 (en) 1973-12-14
DE2221771C3 (en) 1982-05-19
GB1374401A (en) 1974-11-20
CH579030A5 (en) 1976-08-31
DE2221771B2 (en) 1981-07-30
IT986990B (en) 1975-01-30
DE2221771A1 (en) 1973-11-15
IL42152A0 (en) 1973-07-30
BE799032A (en) 1973-11-05
FR2183259B1 (en) 1977-02-11
NL7306266A (en) 1973-11-06
JPS4961120A (en) 1974-06-13

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