DE2300638A1 - Verfahren zur herstellung von 3dimethoxymethyl-glutarsaeuredimethylester und dabei gewonnenes produkt - Google Patents
Verfahren zur herstellung von 3dimethoxymethyl-glutarsaeuredimethylester und dabei gewonnenes produktInfo
- Publication number
- DE2300638A1 DE2300638A1 DE19732300638 DE2300638A DE2300638A1 DE 2300638 A1 DE2300638 A1 DE 2300638A1 DE 19732300638 DE19732300638 DE 19732300638 DE 2300638 A DE2300638 A DE 2300638A DE 2300638 A1 DE2300638 A1 DE 2300638A1
- Authority
- DE
- Germany
- Prior art keywords
- agent
- glutaric acid
- amminolysis
- dimethyl ester
- dimethoxymethyl
- 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
- 238000000034 method Methods 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 238000005915 ammonolysis reaction Methods 0.000 claims description 6
- -1 dimethoxymethyl-glutaric acid dimethyl ester Chemical compound 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- DONPYEFOIBDIJK-UHFFFAOYSA-N COC=C(CC(=O)N)CC(=O)N Chemical compound COC=C(CC(=O)N)CC(=O)N DONPYEFOIBDIJK-UHFFFAOYSA-N 0.000 claims description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002269 spontaneous effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 13
- 239000003054 catalyst Substances 0.000 claims 4
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 238000007098 aminolysis reaction Methods 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- DUAWMBALUQAHRH-UHFFFAOYSA-N dimethyl 3-(dimethoxymethyl)pentanedioate Chemical compound COC(=O)CC(C(OC)OC)CC(=O)OC DUAWMBALUQAHRH-UHFFFAOYSA-N 0.000 claims 1
- UBJGRDQJZTWXDV-UHFFFAOYSA-N dimethyl pentanedioate methanol Chemical compound C(CCCC(=O)OC)(=O)OC.CO UBJGRDQJZTWXDV-UHFFFAOYSA-N 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- RCCYSVYHULFYHE-UHFFFAOYSA-N pentanediamide Chemical compound NC(=O)CCCC(N)=O RCCYSVYHULFYHE-UHFFFAOYSA-N 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 238000003420 transacetalization reaction Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- OQROUFRMUNUJQC-UHFFFAOYSA-N 3-(dimethoxymethyl)pentanediamide Chemical compound COC(OC)C(CC(N)=O)CC(N)=O OQROUFRMUNUJQC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- XSHOQLFLPSMAGQ-UHFFFAOYSA-N octane-2,6-dione Chemical class CCC(=O)CCCC(C)=O XSHOQLFLPSMAGQ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES398690A ES398690A1 (es) | 1972-01-08 | 1972-01-08 | Un procedimiento para la preparacion de 3-dimetoximetilglu-tarato de metilo y su derivado de amonolisis, 3-dimetoxime- tiglutaramida. |
| ES398744A ES398744A1 (es) | 1972-01-11 | 1972-01-11 | Un procedimiento para la preparacion de 3-metoximetilenglu-tarato de metilo y su derivado de amonolisis, 3-metoximeti- lenglutaramida. |
| ES408831A ES408831A1 (es) | 1972-11-21 | 1972-11-21 | Un nuevo procedimiento de obtencion de la 2,8-dioxabiciclo (3.3.0) octano-3,7-diona. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2300638A1 true DE2300638A1 (de) | 1973-08-09 |
Family
ID=27240736
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732300638 Pending DE2300638A1 (de) | 1972-01-08 | 1973-01-08 | Verfahren zur herstellung von 3dimethoxymethyl-glutarsaeuredimethylester und dabei gewonnenes produkt |
| DE2325429*A Pending DE2325429A1 (de) | 1972-01-08 | 1973-01-08 | Dilaktankondensate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2325429*A Pending DE2325429A1 (de) | 1972-01-08 | 1973-01-08 | Dilaktankondensate |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE793720A (enrdf_load_stackoverflow) |
| CH (3) | CH567021A5 (enrdf_load_stackoverflow) |
| DE (2) | DE2300638A1 (enrdf_load_stackoverflow) |
| FR (2) | FR2181651B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1399561A (enrdf_load_stackoverflow) |
| NL (1) | NL7300157A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0257557A3 (en) * | 1986-08-27 | 1989-04-19 | Basf Aktiengesellschaft | Process for the preparation of bifunctional compounds |
| EP0330131A1 (de) * | 1988-02-24 | 1989-08-30 | BASF Aktiengesellschaft | Polycyclische Verbindungen und deren Verwendung |
-
0
- BE BE793720D patent/BE793720A/xx unknown
-
1973
- 1973-01-04 FR FR7300257A patent/FR2181651B1/fr not_active Expired
- 1973-01-05 GB GB81573A patent/GB1399561A/en not_active Expired
- 1973-01-05 NL NL7300157A patent/NL7300157A/xx unknown
- 1973-01-08 DE DE19732300638 patent/DE2300638A1/de active Pending
- 1973-01-08 CH CH1195774A patent/CH567021A5/xx not_active IP Right Cessation
- 1973-01-08 CH CH1195674A patent/CH565744A5/xx not_active IP Right Cessation
- 1973-01-08 DE DE2325429*A patent/DE2325429A1/de active Pending
- 1973-01-08 CH CH14873A patent/CH565743A5/xx not_active IP Right Cessation
- 1973-12-17 FR FR7345063A patent/FR2208900B1/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0257557A3 (en) * | 1986-08-27 | 1989-04-19 | Basf Aktiengesellschaft | Process for the preparation of bifunctional compounds |
| EP0330131A1 (de) * | 1988-02-24 | 1989-08-30 | BASF Aktiengesellschaft | Polycyclische Verbindungen und deren Verwendung |
| US4958022A (en) * | 1988-02-24 | 1990-09-18 | Basf Aktiengesellschaft | Polycyclic compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2325429A1 (de) | 1973-11-08 |
| CH567021A5 (enrdf_load_stackoverflow) | 1975-09-30 |
| FR2181651B1 (enrdf_load_stackoverflow) | 1977-02-04 |
| FR2208900B1 (enrdf_load_stackoverflow) | 1978-01-20 |
| FR2208900A1 (enrdf_load_stackoverflow) | 1974-06-28 |
| FR2181651A1 (enrdf_load_stackoverflow) | 1973-12-07 |
| NL7300157A (enrdf_load_stackoverflow) | 1973-07-10 |
| CH565744A5 (enrdf_load_stackoverflow) | 1975-08-29 |
| BE793720A (fr) | 1973-05-02 |
| GB1399561A (en) | 1975-07-02 |
| CH565743A5 (enrdf_load_stackoverflow) | 1975-08-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0092814B1 (de) | Neue Zwischenprodukte zur Herstellung N-Alkylnorscopine, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2166657C2 (enrdf_load_stackoverflow) | ||
| DE2300638A1 (de) | Verfahren zur herstellung von 3dimethoxymethyl-glutarsaeuredimethylester und dabei gewonnenes produkt | |
| DE2654928C3 (de) | Verfahren zur Herstellung von N-methylierten Harnstoffen oder Alkylenharnstoffen | |
| DE824635C (de) | Verfahren zur Herstellung von N-Carboanhydriden | |
| DE3830351A1 (de) | Verfahren zur herstellung von (alpha)-aminoalkanolen | |
| DE2409675A1 (de) | Alpha-alkyl(oder -aryl)-thio-5-hydroxytryptophan-derivat und verfahren zu seiner herstellung | |
| DE10019291C2 (de) | 2-Alkoxy-5-methoxypyrimidine bzw. deren tautomere Formen sowie Verfahren zu deren Herstellung | |
| CH409903A (de) | Verfahren zur Herstellung von organischen Fluor-Verbindungen | |
| DE68917994T2 (de) | Verfahren zur Herstellung von Pyrrolizinderivaten. | |
| DE2024805C3 (de) | Verfahren zur Herstellung von 2-Amino-3-chlorpyrazin | |
| DE2345060A1 (de) | 1,2-dialkylketonglycerin-3-phosphatide und verfahren zu deren herstellung | |
| DE942149C (de) | Verfahren zur Herstellung substituierter Glycinamide | |
| DE1046063B (de) | Verfahren zur Herstellung neuer, amoebicid wirkender Acetanilide | |
| DE2747472A1 (de) | Verfahren zur herstellung von natrium-alkoxycarbonylcyanamiden | |
| AT313298B (de) | Verfahren zur Herstellung von neuen Pyrrolidin-N-carbonsäure-halogenaniliden | |
| AT359989B (de) | Verfahren zur herstellung von neuen omega- -amino-carbonsaeureamiden und von deren salzen | |
| AT367411B (de) | Verfahren zur herstellung von neuen 4-amino-1,2kohlenwasserstoffsubstituierten-pyrazolidinen und von deren salzen | |
| DE1950075C2 (de) | Verfahren zur Herstellung von 4-Chlorpyrazolo- eckige Klammer auf 3,4-d eckige Klammer zu pyrimidin | |
| DE2718084C2 (enrdf_load_stackoverflow) | ||
| DE1420954C (de) | Halogensubstituierte 5-Phenyl-2-aminooxazolon-(4)-derivate und Verfahren zu deren Herstellung | |
| DE2757586A1 (de) | Natrium-formylcyanamid und verfahren zu seiner herstellung | |
| DE2328870A1 (de) | Dihalogenazyldiazepinderivate und verfahren zu ihrer herstellung | |
| DE1922802A1 (de) | Verfahren zur Herstellung von cyclischen Formamidinen | |
| DE2023429A1 (de) | Verfahren zur Herstellung von Dialkylformamid-Derivaten |