BE459304A - - Google Patents

Info

Publication number

BE459304A

BE459304A BE459304DA BE459304A BE 459304 A BE459304 A BE 459304A BE 459304D A BE459304D A BE 459304DA BE 459304 A BE459304 A BE 459304A

Authority

BE

Belgium

Prior art keywords

parts

diacetyl

diketones

desc

aliphatic

Prior art date

Links

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• 239000007859 condensation product Substances 0.000 claims description 10
• 125000001931 aliphatic group Chemical group 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000003118 aryl group Chemical group 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 2
• QSJXEFYPDANLFS-UHFFFAOYSA-N diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 8
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
• 229960004050 aminobenzoic acid Drugs 0.000 description 4
• 238000000034 method Methods 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
• ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-Aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
• BZORFPDSXLZWJF-UHFFFAOYSA-N Dimethyl-4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• QSNSCYSYFYORTR-UHFFFAOYSA-N 4-Chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
• -1 @ p-aminophenol Chemical compound 0.000 description 2
• 210000004940 Nucleus Anatomy 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
• 230000000844 anti-bacterial Effects 0.000 description 2
• 150000001875 compounds Chemical class 0.000 description 2
• 125000005594 diketone group Chemical group 0.000 description 2
• TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical group CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• JOLPMPPNHIACPD-ZZXKWVIFSA-N (E)-3-(4-aminophenyl)prop-2-enoic acid Chemical compound NC1=CC=C(\C=C\C(O)=O)C=C1 JOLPMPPNHIACPD-ZZXKWVIFSA-N 0.000 description 1
• MELCWEWUZODSIS-UHFFFAOYSA-N 2-[2-(diethylamino)ethoxy]-N,N-diethylethanamine Chemical class CCN(CC)CCOCCN(CC)CC MELCWEWUZODSIS-UHFFFAOYSA-N 0.000 description 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
• QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-N,4-N-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
• JENYBWHRLYZSSZ-UHFFFAOYSA-N 4-methylpentane-2,3-dione Chemical group CC(C)C(=O)C(C)=O JENYBWHRLYZSSZ-UHFFFAOYSA-N 0.000 description 1
• 241001606065 Aoa Species 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 238000007792 addition Methods 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 150000001412 amines Chemical class 0.000 description 1
• 244000052616 bacterial pathogens Species 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 159000000007 calcium salts Chemical class 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 230000000875 corresponding Effects 0.000 description 1
• 201000009910 diseases by infectious agent Diseases 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• KVFQMAZOBTXCAZ-UHFFFAOYSA-N hexane-3,4-dione Chemical group CCC(=O)C(=O)CC KVFQMAZOBTXCAZ-UHFFFAOYSA-N 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 230000001376 precipitating Effects 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 235000011121 sodium hydroxide Nutrition 0.000 description 1
• 159000000000 sodium salts Chemical class 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 201000008827 tuberculosis Diseases 0.000 description 1