CH438357A - Verfahren zur Herstellung von N,N'-Dibenzoyldiarylaminophthalsäuredialkylestern - Google Patents
Verfahren zur Herstellung von N,N'-DibenzoyldiarylaminophthalsäuredialkylesternInfo
- Publication number
- CH438357A CH438357A CH134663A CH134663A CH438357A CH 438357 A CH438357 A CH 438357A CH 134663 A CH134663 A CH 134663A CH 134663 A CH134663 A CH 134663A CH 438357 A CH438357 A CH 438357A
- Authority
- CH
- Switzerland
- Prior art keywords
- ouzo
- dimethyl ester
- parts
- acid dimethyl
- bis
- Prior art date
Links
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 54
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000002253 acid Substances 0.000 title description 9
- 150000002148 esters Chemical class 0.000 title description 9
- -1 heterocyclic radicals Chemical class 0.000 claims description 22
- 230000008707 rearrangement Effects 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000002170 ethers Chemical class 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 235000020075 ouzo Nutrition 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 6
- WFFOTOYJOIXKCA-UHFFFAOYSA-N dimethyl 2,4-dihydroxybenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=C(O)C(C(=O)OC)=C1O WFFOTOYJOIXKCA-UHFFFAOYSA-N 0.000 description 5
- WABMHCVYKWKAAH-UHFFFAOYSA-N dimethyl 2,5-dihydroxybenzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC(O)=C(C(=O)OC)C=C1O WABMHCVYKWKAAH-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QXGJCWSBOZXWOV-UHFFFAOYSA-N 3,4-dihydroxyphthalic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1C(O)=O QXGJCWSBOZXWOV-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 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 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- STWMCBFQCITJQM-UHFFFAOYSA-N dimethyl 2,3-dihydroxybenzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(O)=C1O STWMCBFQCITJQM-UHFFFAOYSA-N 0.000 description 3
- CMTOZSKJCALTLF-UHFFFAOYSA-N dimethyl 4,6-dihydroxybenzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=C(O)C=C1O CMTOZSKJCALTLF-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- FYWWCUGVUUAPRV-UHFFFAOYSA-N COC(C(C=C(C(C(OC)=O)=C1)N(C(C2=CC=CC=C2)=O)C2=CC=CC=C2)=C1N(C(C1=CC=CC=C1)=O)C1=CC=CC=C1)=O Chemical compound COC(C(C=C(C(C(OC)=O)=C1)N(C(C2=CC=CC=C2)=O)C2=CC=CC=C2)=C1N(C(C1=CC=CC=C1)=O)C1=CC=CC=C1)=O FYWWCUGVUUAPRV-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003902 salicylic acid esters Chemical class 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZJQZWNLKRBUEKX-UHFFFAOYSA-N 2,5-dianilinoterephthalic acid Chemical compound OC(=O)C=1C=C(NC=2C=CC=CC=2)C(C(=O)O)=CC=1NC1=CC=CC=C1 ZJQZWNLKRBUEKX-UHFFFAOYSA-N 0.000 description 1
- TUAMYQPQAXKOQN-UHFFFAOYSA-N 2-(n-benzoylanilino)benzoic acid Chemical class OC(=O)C1=CC=CC=C1N(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 TUAMYQPQAXKOQN-UHFFFAOYSA-N 0.000 description 1
- MZGVIIXFGJCRDR-UHFFFAOYSA-N 4,6-dihydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(O)C=C1O MZGVIIXFGJCRDR-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- HKSUFSHKTCVIIP-UHFFFAOYSA-N COC(=O)C1=C(O)CC(O)(C(=O)OC)C=C1 Chemical compound COC(=O)C1=C(O)CC(O)(C(=O)OC)C=C1 HKSUFSHKTCVIIP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- WOZVHXUHUFLZGK-UHFFFAOYSA-N terephthalic acid dimethyl ester Natural products COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB65915A DE1185621B (de) | 1962-02-13 | 1962-02-13 | Verfahren zur Herstellung von N, N'-Dibenzoyldiarylamino-phthalsaeuredialkylestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH438357A true CH438357A (de) | 1967-06-30 |
Family
ID=6974950
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH134663A CH438357A (de) | 1962-02-13 | 1963-02-04 | Verfahren zur Herstellung von N,N'-Dibenzoyldiarylaminophthalsäuredialkylestern |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE628295A (en]) |
| CH (1) | CH438357A (en]) |
| DE (1) | DE1185621B (en]) |
| GB (1) | GB1025910A (en]) |
-
0
- BE BE628295D patent/BE628295A/xx unknown
-
1962
- 1962-02-13 DE DEB65915A patent/DE1185621B/de active Pending
-
1963
- 1963-02-04 CH CH134663A patent/CH438357A/de unknown
- 1963-02-06 GB GB477663A patent/GB1025910A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1025910A (en) | 1966-04-14 |
| DE1185621B (de) | 1965-01-21 |
| BE628295A (en]) |
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