DE294085A - - Google Patents

Info

Publication number

DE294085A

DE294085A DE294085A DE 294085 A DE294085 A DE 294085A DE 294085 A DE294085 A DE 294085A

Authority

DE

Germany

Prior art keywords

water

benzene

parts

alcohol

nitro

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

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• 150000001556 benzimidazoles Chemical class 0.000 claims description 5
• 238000000034 method Methods 0.000 claims description 4
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
• XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• 229960000583 acetic acid Drugs 0.000 description 8
• 239000000155 melt Substances 0.000 description 8
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
• 239000002253 acid Substances 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• 239000012362 glacial acetic acid Substances 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• 125000003277 amino group Chemical group 0.000 description 3
• 150000001875 compounds Chemical class 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 229910052742 iron Inorganic materials 0.000 description 3
• JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• 150000002460 imidazoles Chemical class 0.000 description 2
• 229910017604 nitric acid Inorganic materials 0.000 description 2
• 150000002828 nitro derivatives Chemical class 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
• 230000001766 physiological effect Effects 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• HTFQXLGSPSJSGC-UHFFFAOYSA-N 4-(4-aminoanilino)butan-2-one Chemical compound CC(=O)CCNC1=CC=C(N)C=C1 HTFQXLGSPSJSGC-UHFFFAOYSA-N 0.000 description 1
• -1 4-formylamino-3-nitrophenylacetylamine Chemical compound 0.000 description 1
• SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
• JDNFGNIUEHOZCP-UHFFFAOYSA-N 6-ethoxy-2-methyl-1h-benzimidazole Chemical compound CCOC1=CC=C2N=C(C)NC2=C1 JDNFGNIUEHOZCP-UHFFFAOYSA-N 0.000 description 1
• RMUCZJUITONUFY-UHFFFAOYSA-N Phenelzine Chemical compound NNCCC1=CC=CC=C1 RMUCZJUITONUFY-UHFFFAOYSA-N 0.000 description 1
• 230000021736 acetylation Effects 0.000 description 1
• 238000006640 acetylation reaction Methods 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 125000003118 aryl group Chemical group 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 229940079593 drug Drugs 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• XCAJEXZWARSCGJ-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]acetamide Chemical compound CC(=O)NCCC1=CC=C(N)C=C1 XCAJEXZWARSCGJ-UHFFFAOYSA-N 0.000 description 1
• WOECBVIBQKTQTO-UHFFFAOYSA-N n-ethyl-2-methyl-3h-benzimidazol-5-amine Chemical compound CCNC1=CC=C2N=C(C)NC2=C1 WOECBVIBQKTQTO-UHFFFAOYSA-N 0.000 description 1
• IUNSCUJDXYSUPK-UHFFFAOYSA-N n-ethyl-3h-benzimidazol-5-amine Chemical compound CCNC1=CC=C2N=CNC2=C1 IUNSCUJDXYSUPK-UHFFFAOYSA-N 0.000 description 1
• 230000000802 nitrating effect Effects 0.000 description 1
• 239000001048 orange dye 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
• QXDAEKSDNVPFJG-UHFFFAOYSA-N phenacaine Chemical compound C1=CC(OCC)=CC=C1N\C(C)=N\C1=CC=C(OCC)C=C1 QXDAEKSDNVPFJG-UHFFFAOYSA-N 0.000 description 1
• 229950007049 phenacaine Drugs 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 239000000725 suspension Substances 0.000 description 1