IL42152A - The production of alpha-iminonitriles - Google Patents
The production of alpha-iminonitrilesInfo
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 238000000034 method Methods 0.000 claims 16
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 6
- 229910052751 metal Inorganic materials 0.000 claims 6
- 239000002184 metal Substances 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 3
- -1 imide halide Chemical class 0.000 claims 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000001302 tertiary amino group Chemical group 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
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)
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 -
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)
| 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 |
-
1972
- 1972-05-04 DE DE2221771A patent/DE2221771C3/en not_active Expired
-
1973
- 1973-05-01 IL IL42152A patent/IL42152A/en unknown
- 1973-05-02 IT IT23637/73A patent/IT986990B/en active
- 1973-05-02 CH CH626073A patent/CH579030A5/xx not_active IP Right Cessation
- 1973-05-03 GB GB2107873A patent/GB1374401A/en not_active Expired
- 1973-05-03 BE BE130687A patent/BE799032A/en unknown
- 1973-05-04 NL NL7306266A patent/NL7306266A/xx not_active Application Discontinuation
- 1973-05-04 JP JP48049173A patent/JPS4961120A/ja active Pending
- 1973-05-04 FR FR7316086A patent/FR2183259B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4961120A (en) | 1974-06-13 |
| DE2221771A1 (en) | 1973-11-15 |
| FR2183259A1 (en) | 1973-12-14 |
| NL7306266A (en) | 1973-11-06 |
| DE2221771B2 (en) | 1981-07-30 |
| DE2221771C3 (en) | 1982-05-19 |
| FR2183259B1 (en) | 1977-02-11 |
| IT986990B (en) | 1975-01-30 |
| BE799032A (en) | 1973-11-05 |
| GB1374401A (en) | 1974-11-20 |
| IL42152A0 (en) | 1973-07-30 |
| CH579030A5 (en) | 1976-08-31 |
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