ATE39T1 - PROCESS FOR THE PREPARATION OF O-METHYL-N-CYCLOHEXYL-2,5-DIMETHYLFURAN-3-HYDROXAMIC ACID. - Google Patents
PROCESS FOR THE PREPARATION OF O-METHYL-N-CYCLOHEXYL-2,5-DIMETHYLFURAN-3-HYDROXAMIC ACID.Info
- Publication number
- ATE39T1 ATE39T1 AT79101422T AT79101422T ATE39T1 AT E39 T1 ATE39 T1 AT E39T1 AT 79101422 T AT79101422 T AT 79101422T AT 79101422 T AT79101422 T AT 79101422T AT E39 T1 ATE39 T1 AT E39T1
- Authority
- AT
- Austria
- Prior art keywords
- dimethylfuran
- cyclohexyl
- hydroxamic acid
- methyl
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- QTDRLOKFLJJHTG-UHFFFAOYSA-N Furmecyclox Chemical compound C1=C(C)OC(C)=C1C(=O)N(OC)C1CCCCC1 QTDRLOKFLJJHTG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- RWORXZHVOUPMMM-UHFFFAOYSA-N 2,5-dimethylfuran-3-carbonyl chloride Chemical compound CC1=CC(C(Cl)=O)=C(C)O1 RWORXZHVOUPMMM-UHFFFAOYSA-N 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- GUQRKZPMVLRXLT-UHFFFAOYSA-N n-cyclohexylhydroxylamine Chemical compound ONC1CCCCC1 GUQRKZPMVLRXLT-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- -1 alkali metal salt Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 230000001035 methylating effect Effects 0.000 abstract 1
- XDFYQYACWQRAIV-UHFFFAOYSA-N n-cyclohexyl-n-hydroxy-2,5-dimethylfuran-3-carboxamide Chemical compound O1C(C)=CC(C(=O)N(O)C2CCCCC2)=C1C XDFYQYACWQRAIV-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
Classifications
-
- 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Abstract
1. A process for the preparation of 0-methyl-N-cyclohexyl-2,5-dimethylfuran-3-hydroxamic acid by reacting N-cyclohexylhydroxylamine or its hydrochloride with 2,5-dimethylfuran-3-carboxylic acid chloride in the presence of an organic solvent and of an alkaline compound and methylating the hydroxamic acid in the presence of water and alkali, characterized in that N-cyclohexylhydroxylamine is reacted with 2,5-dimethylfuran-3-carboxylic acid chloride in the presence of water, a liquid hydrocarbon and an inorganic alkaline compound, the resulting N-cyclohexyl-2,5-dimethylfuran-3-hydroxamic acid is converted, by treating the reaction mixture with an aqueous alkali metal hydroxide solution, to an aqueous solution of its alkali metal salt, the compound is then methylated in this solution and the 0-methyl-N-cyclohexyl-2,5-dimethylfuran-3-hydroxamic acid thus prepared is isolated from the aqueous solution by means of a water-immiscible organic solvent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782821087 DE2821087A1 (en) | 1978-05-13 | 1978-05-13 | PROCESS FOR THE PREPARATION OF 0-METHYL-N-CYCLOHEXYL-2,5-DI-METHYLFURAN-3-HYDROXAMIC ACID |
| EP79101422A EP0005509B1 (en) | 1978-05-13 | 1979-05-10 | Process for the preparation of o-methyl-n-cyclohexyl-2,5-dimethyl-3-furanhydroxamic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE39T1 true ATE39T1 (en) | 1981-05-15 |
Family
ID=6039341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT79101422T ATE39T1 (en) | 1978-05-13 | 1979-05-10 | PROCESS FOR THE PREPARATION OF O-METHYL-N-CYCLOHEXYL-2,5-DIMETHYLFURAN-3-HYDROXAMIC ACID. |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0005509B1 (en) |
| AT (1) | ATE39T1 (en) |
| DE (2) | DE2821087A1 (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3778512A (en) * | 1970-06-23 | 1973-12-11 | Velsicol Chemical Corp | Fungicidal method utilizing furancarboxamides |
-
1978
- 1978-05-13 DE DE19782821087 patent/DE2821087A1/en active Pending
-
1979
- 1979-05-10 EP EP79101422A patent/EP0005509B1/en not_active Expired
- 1979-05-10 DE DE7979101422T patent/DE2960264D1/en not_active Expired
- 1979-05-10 AT AT79101422T patent/ATE39T1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0005509B1 (en) | 1981-04-15 |
| DE2821087A1 (en) | 1979-11-22 |
| EP0005509A3 (en) | 1979-12-12 |
| EP0005509A2 (en) | 1979-11-28 |
| DE2960264D1 (en) | 1981-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| REN | Ceased due to non-payment of the annual fee |