DE112174C - - Google Patents
Info
- Publication number
- DE112174C DE112174C DE1899112174D DE112174DA DE112174C DE 112174 C DE112174 C DE 112174C DE 1899112174 D DE1899112174 D DE 1899112174D DE 112174D A DE112174D A DE 112174DA DE 112174 C DE112174 C DE 112174C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- oxane
- amino
- aminophenyltartronic
- alcohol
- 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.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 claims description 31
- -1 p-ethylamino-m-toluyltartronic acid Chemical compound 0.000 claims description 15
- HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 claims description 14
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- IFTYZLXVLABQIZ-UHFFFAOYSA-N 2-aminooxy-2-phenylpropanedioic acid Chemical class NOC(C(=O)O)(C(=O)O)C1=CC=CC=C1 IFTYZLXVLABQIZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 7
- KIYFBJUYUZJZKK-UHFFFAOYSA-N NC1=CC=C(C=C1)C(C(=O)O)(O)C(=O)O Chemical compound NC1=CC=C(C=C1)C(C(=O)O)(O)C(=O)O KIYFBJUYUZJZKK-UHFFFAOYSA-N 0.000 claims description 5
- QQFDFQMQRSTFJW-UHFFFAOYSA-N NC1=CC=CC=C1.O1CCCCC1 Chemical compound NC1=CC=CC=C1.O1CCCCC1 QQFDFQMQRSTFJW-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- DDJUZGWGNDLZQR-UHFFFAOYSA-N NC1=C(C=C(C=C1)C)C(C(=O)O)(O)C(=O)O Chemical compound NC1=C(C=C(C=C1)C)C(C(=O)O)(O)C(=O)O DDJUZGWGNDLZQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- FWSYUFPTTJWRFL-UHFFFAOYSA-N 2-(4-amino-3-ethoxyphenyl)-2-hydroxypropanedioic acid Chemical compound CCOC1=CC(C(O)(C(O)=O)C(O)=O)=CC=C1N FWSYUFPTTJWRFL-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- LUETYUCYTZWNQD-UHFFFAOYSA-N CNC1=CC=C(C=C1)C(C(=O)O)(O)C(=O)O Chemical compound CNC1=CC=C(C=C1)C(C(=O)O)(O)C(=O)O LUETYUCYTZWNQD-UHFFFAOYSA-N 0.000 claims 1
- SMIWQQBDXYQJND-UHFFFAOYSA-N CNC1=CC=CC=C1.O1CCCCC1 Chemical compound CNC1=CC=CC=C1.O1CCCCC1 SMIWQQBDXYQJND-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- 238000009835 boiling Methods 0.000 description 12
- 238000005187 foaming Methods 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000155 melt Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- 150000001447 alkali salts Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000219492 Quercus Species 0.000 description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008043 acidic salts Chemical class 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- FRWLWDNANOVSOK-UHFFFAOYSA-N 2-hydroxy-2-phenylpropanedioic acid Chemical compound OC(=O)C(O)(C(O)=O)C1=CC=CC=C1 FRWLWDNANOVSOK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000005586 carbonic acid group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- ROBFUDYVXSDBQM-UHFFFAOYSA-N hydroxymalonic acid Chemical group OC(=O)C(O)C(O)=O ROBFUDYVXSDBQM-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- XEEVLJKYYUVTRC-UHFFFAOYSA-N oxomalonic acid Chemical group OC(=O)C(=O)C(O)=O XEEVLJKYYUVTRC-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT4094D AT4094B (forum.php) | 1899-03-25 | 1900-07-03 | |
| AT7847D AT7847B (de) | 1899-03-25 | 1901-06-15 | Verfahren zur Darstellung von Aminophenyltartronsäuren. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE112174C true DE112174C (forum.php) |
Family
ID=381855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1899112174D Expired - Lifetime DE112174C (forum.php) | 1899-03-25 | 1899-03-25 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE112174C (forum.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0223037A1 (de) * | 1985-10-24 | 1987-05-27 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Phenylbarbitursäuren und deren Herstellung |
-
1899
- 1899-03-25 DE DE1899112174D patent/DE112174C/de not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0223037A1 (de) * | 1985-10-24 | 1987-05-27 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Phenylbarbitursäuren und deren Herstellung |
| US4775756A (en) * | 1985-10-24 | 1988-10-04 | Hoffmann-La Roche Inc. | 5-(4-amino-3,5-dimethoxyphenyl)-5-hydroxy-barbituric acid |
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