CH630339A5 - Verfahren zur herstellung von enamiden. - Google Patents
Verfahren zur herstellung von enamiden. Download PDFInfo
- Publication number
- CH630339A5 CH630339A5 CH540077A CH540077A CH630339A5 CH 630339 A5 CH630339 A5 CH 630339A5 CH 540077 A CH540077 A CH 540077A CH 540077 A CH540077 A CH 540077A CH 630339 A5 CH630339 A5 CH 630339A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- chem
- ruthenium
- mol
- alkyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000003054 catalyst Substances 0.000 claims description 17
- -1 N-acylimidazolyl Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 150000002923 oximes Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000005610 enamide group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229910052707 ruthenium Inorganic materials 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- NCPHGZWGGANCAY-UHFFFAOYSA-N methane;ruthenium Chemical compound C.[Ru] NCPHGZWGGANCAY-UHFFFAOYSA-N 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 2
- UBADKKCCQHYPIX-UHFFFAOYSA-N aluminum oxygen(2-) ruthenium(3+) Chemical compound [O-2].[Al+3].[Ru+3].[O-2].[O-2] UBADKKCCQHYPIX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 244000309464 bull Species 0.000 claims 2
- 238000006237 Beckmann rearrangement reaction Methods 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 150000003862 amino acid derivatives Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000009102 absorption Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 3
- MDLJMYBJBOYUNJ-KTKRTIGZSA-N (nz)-n-(1-phenylpropylidene)hydroxylamine Chemical compound CC\C(=N\O)C1=CC=CC=C1 MDLJMYBJBOYUNJ-KTKRTIGZSA-N 0.000 description 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- PWDNIJDAAHENOW-UHFFFAOYSA-N n-acetyl-n-(cyclohexen-1-yl)acetamide Chemical compound CC(=O)N(C(C)=O)C1=CCCCC1 PWDNIJDAAHENOW-UHFFFAOYSA-N 0.000 description 2
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CFGYUVCPXSZUQM-UHFFFAOYSA-N (2-acetamido-1,2-diphenylethenyl) acetate Chemical group C=1C=CC=CC=1C(NC(=O)C)=C(OC(C)=O)C1=CC=CC=C1 CFGYUVCPXSZUQM-UHFFFAOYSA-N 0.000 description 1
- JAUFWTSSYRTLLB-UHFFFAOYSA-N (2-phenylacetyl) 2-phenylacetate Chemical compound C=1C=CC=CC=1CC(=O)OC(=O)CC1=CC=CC=C1 JAUFWTSSYRTLLB-UHFFFAOYSA-N 0.000 description 1
- WAKHLWOJMHVUJC-FYWRMAATSA-N (2e)-2-hydroxyimino-1,2-diphenylethanol Chemical compound C=1C=CC=CC=1C(=N/O)\C(O)C1=CC=CC=C1 WAKHLWOJMHVUJC-FYWRMAATSA-N 0.000 description 1
- JHNRZXQVBKRYKN-VQHVLOKHSA-N (ne)-n-(1-phenylethylidene)hydroxylamine Chemical compound O\N=C(/C)C1=CC=CC=C1 JHNRZXQVBKRYKN-VQHVLOKHSA-N 0.000 description 1
- IFDZZSXEPSSHNC-ARJAWSKDSA-N (nz)-n-propylidenehydroxylamine Chemical compound CC\C=N/O IFDZZSXEPSSHNC-ARJAWSKDSA-N 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
- HOHYEIQWWGPNPX-UHFFFAOYSA-N 2-hydroxyimino-3-(1h-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CC(=NO)C(O)=O)=CNC2=C1 HOHYEIQWWGPNPX-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- FREZLSIGWNCSOQ-UHFFFAOYSA-N 3-methylbutanoyl 3-methylbutanoate Chemical compound CC(C)CC(=O)OC(=O)CC(C)C FREZLSIGWNCSOQ-UHFFFAOYSA-N 0.000 description 1
- 101100459439 Caenorhabditis elegans nac-2 gene Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- WRAGCBBWIYQMRF-UHFFFAOYSA-N N-Cyclohexylacetamide Chemical compound CC(=O)NC1CCCCC1 WRAGCBBWIYQMRF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BLKCFLMAFZMUQE-UHFFFAOYSA-N [2-(diacetylamino)-1,2-diphenylethenyl] acetate Chemical group C=1C=CC=CC=1C(OC(=O)C)=C(N(C(C)=O)C(C)=O)C1=CC=CC=C1 BLKCFLMAFZMUQE-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- WAKHLWOJMHVUJC-UHFFFAOYSA-N benzoin alpha-oxime Natural products C=1C=CC=CC=1C(=NO)C(O)C1=CC=CC=C1 WAKHLWOJMHVUJC-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- BJBDPHKMAMMTFW-UHFFFAOYSA-N ethyl 2-hydroxyiminopropanoate Chemical compound CCOC(=O)C(C)=NO BJBDPHKMAMMTFW-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HMHNYSRISCEVNV-UHFFFAOYSA-N methyl 2-hydroxyimino-4-methylpentanoate Chemical compound COC(=O)C(=NO)CC(C)C HMHNYSRISCEVNV-UHFFFAOYSA-N 0.000 description 1
- PWCUVRROUAKTLL-UHFFFAOYSA-N n-(1,2-diphenylethylidene)hydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)CC1=CC=CC=C1 PWCUVRROUAKTLL-UHFFFAOYSA-N 0.000 description 1
- YDQLQCOYQHAGDV-UHFFFAOYSA-N n-(2-hydroxy-1,2-diphenylethenyl)acetamide Chemical group C=1C=CC=CC=1C(NC(=O)C)=C(O)C1=CC=CC=C1 YDQLQCOYQHAGDV-UHFFFAOYSA-N 0.000 description 1
- RKDAPIXTZRTFKL-UHFFFAOYSA-N n-(cyclohexen-1-yl)acetamide Chemical compound CC(=O)NC1=CCCCC1 RKDAPIXTZRTFKL-UHFFFAOYSA-N 0.000 description 1
- VKAVIFFNMYKZBP-UHFFFAOYSA-N n-acetyl-n-(2-hydroxy-1,2-diphenylethenyl)acetamide Chemical group C=1C=CC=CC=1C(N(C(C)=O)C(=O)C)=C(O)C1=CC=CC=C1 VKAVIFFNMYKZBP-UHFFFAOYSA-N 0.000 description 1
- RVBDIVPROLVQTN-UHFFFAOYSA-N n-acetyl-n-prop-1-enylacetamide Chemical compound CC=CN(C(C)=O)C(C)=O RVBDIVPROLVQTN-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- VZWXZWNGJLFHRY-UHFFFAOYSA-N propyl 2-hydroxyimino-3-methylbutanoate Chemical compound CCCOC(=O)C(=NO)C(C)C VZWXZWNGJLFHRY-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229950005792 tenoate Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5053776A JPS52133905A (en) | 1976-04-30 | 1976-04-30 | Preparation of enamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH630339A5 true CH630339A5 (de) | 1982-06-15 |
Family
ID=12861746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH540077A CH630339A5 (de) | 1976-04-30 | 1977-04-29 | Verfahren zur herstellung von enamiden. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4137417A (Direct) |
| JP (1) | JPS52133905A (Direct) |
| CH (1) | CH630339A5 (Direct) |
| DE (1) | DE2718552C2 (Direct) |
| FR (1) | FR2349567A1 (Direct) |
| GB (1) | GB1526683A (Direct) |
| IT (1) | IT1080382B (Direct) |
| NL (1) | NL7704627A (Direct) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4490167A (en) * | 1979-08-06 | 1984-12-25 | Ciba-Geigy Corporation | Oxime derivatives of diphenyl ethers and their use in herbicidal compositions |
| JPS584748A (ja) * | 1981-06-30 | 1983-01-11 | Takasago Corp | エナミンまたはイミンの製造方法 |
| US4996348A (en) * | 1987-07-29 | 1991-02-26 | Ciba-Geigy Corporation | N-alkenoyl enamides, their preparation and the use thereof |
| US5559268A (en) * | 1994-11-17 | 1996-09-24 | E. I. Du Pont De Nemours And Company | Process for the efficient preparation of N-substituted dehydroamino acid esters |
| EP1547997A1 (en) * | 2003-12-22 | 2005-06-29 | Ppg - Sipsy | New process for the synthesis of enamide derivatives |
| PT2816024T (pt) * | 2006-03-31 | 2017-10-20 | Sunovion Pharmaceuticals Inc | Aminas quirais |
| KR102502637B1 (ko) * | 2018-05-14 | 2023-02-22 | 미쓰이 가가쿠 가부시키가이샤 | 에피설파이드계 광학재료용 모노머의 몰드 자동 주입방법 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4055512A (en) * | 1974-05-09 | 1977-10-25 | Mitsubishi Chemical Industries Ltd. | Catalyst for producing cycloolefin and method for making the same |
| DE2502894C3 (de) * | 1975-01-24 | 1981-12-03 | Bayer Ag, 5090 Leverkusen | Ruthenium-Trägerkatalysator |
-
1976
- 1976-04-30 JP JP5053776A patent/JPS52133905A/ja active Granted
-
1977
- 1977-04-26 DE DE2718552A patent/DE2718552C2/de not_active Expired
- 1977-04-26 US US05/790,908 patent/US4137417A/en not_active Expired - Lifetime
- 1977-04-27 NL NL7704627A patent/NL7704627A/xx not_active Application Discontinuation
- 1977-04-27 GB GB17665/77A patent/GB1526683A/en not_active Expired
- 1977-04-29 IT IT23015/77A patent/IT1080382B/it active
- 1977-04-29 CH CH540077A patent/CH630339A5/de not_active IP Right Cessation
- 1977-04-29 FR FR7713072A patent/FR2349567A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2718552A1 (de) | 1977-11-10 |
| JPS52133905A (en) | 1977-11-09 |
| US4137417A (en) | 1979-01-30 |
| NL7704627A (nl) | 1977-11-01 |
| GB1526683A (en) | 1978-09-27 |
| FR2349567A1 (fr) | 1977-11-25 |
| DE2718552C2 (de) | 1986-11-27 |
| FR2349567B1 (Direct) | 1980-08-01 |
| JPS616812B2 (Direct) | 1986-03-01 |
| IT1080382B (it) | 1985-05-16 |
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