BE503013A - - Google Patents

Info

Publication number

BE503013A

BE503013A BE503013DA BE503013A BE 503013 A BE503013 A BE 503013A BE 503013D A BE503013D A BE 503013DA BE 503013 A BE503013 A BE 503013A

Authority

BE

Belgium

Prior art keywords

alcohol

thiosemicarbazide

solution

heated

reflux

Prior art date

Links

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• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 3
• -1 thiosemicarbazide hydroxybenzaldehydes Chemical class 0.000 claims description 2
• 150000003583 thiosemicarbazides Chemical class 0.000 claims description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
• BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 8
• 238000010992 reflux Methods 0.000 description 7
• 150000001875 compounds Chemical class 0.000 description 6
• 238000010438 heat treatment Methods 0.000 description 6
• 238000002844 melting Methods 0.000 description 6
• 230000008018 melting Effects 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
• 229960000583 acetic acid Drugs 0.000 description 5
• 239000012362 glacial acetic acid Substances 0.000 description 5
• IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
• RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
• 239000013078 crystal Substances 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 235000011121 sodium hydroxide Nutrition 0.000 description 4
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
• 229910052753 mercury Inorganic materials 0.000 description 3
• 229910000027 potassium carbonate Inorganic materials 0.000 description 3
• 239000002244 precipitate Substances 0.000 description 3
• AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 description 2
• 230000001476 alcoholic effect Effects 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 229940046892 lead acetate Drugs 0.000 description 2
• LJVHJHLTRBXGMH-HNQUOIGGSA-N (e)-1,4-dibromobut-1-ene Chemical compound BrCC\C=C\Br LJVHJHLTRBXGMH-HNQUOIGGSA-N 0.000 description 1
• WFJFGMLKAISFOZ-UHFFFAOYSA-N 1-amino-3-iminourea Chemical compound NN=C(O)N=N WFJFGMLKAISFOZ-UHFFFAOYSA-N 0.000 description 1
• QRDVXBUAVNLNSJ-UHFFFAOYSA-N 3-but-2-enoxybenzaldehyde Chemical compound CC=CCOC1=CC=CC(C=O)=C1 QRDVXBUAVNLNSJ-UHFFFAOYSA-N 0.000 description 1
• SEDRQGRABDFZKO-UHFFFAOYSA-N 3-prop-2-enoxybenzaldehyde Chemical compound C=CCOC1=CC=CC(C=O)=C1 SEDRQGRABDFZKO-UHFFFAOYSA-N 0.000 description 1
• GJTUFKFMBKCFIH-UHFFFAOYSA-N 4-but-2-enoxybenzaldehyde Chemical compound CC=CCOC1=CC=C(C=O)C=C1 GJTUFKFMBKCFIH-UHFFFAOYSA-N 0.000 description 1
• TYNJQOJWNMZQFZ-UHFFFAOYSA-N 4-prop-2-enoxybenzaldehyde Chemical compound C=CCOC1=CC=C(C=O)C=C1 TYNJQOJWNMZQFZ-UHFFFAOYSA-N 0.000 description 1
• GSSBOYWRKTVVQX-UHFFFAOYSA-N 4-prop-2-ynoxybenzaldehyde Chemical compound O=CC1=CC=C(OCC#C)C=C1 GSSBOYWRKTVVQX-UHFFFAOYSA-N 0.000 description 1
• ZPDCCOTYWBACPZ-UHFFFAOYSA-N [K].OC1=CC=C(C=O)C=C1 Chemical compound [K].OC1=CC=C(C=O)C=C1 ZPDCCOTYWBACPZ-UHFFFAOYSA-N 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
• 230000003110 anti-inflammatory effect Effects 0.000 description 1
• 230000002558 anti-leprotic effect Effects 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 150000007857 hydrazones Chemical class 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 150000002923 oximes Chemical class 0.000 description 1
• YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
• 239000011541 reaction mixture Substances 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
• 150000003584 thiosemicarbazones Chemical class 0.000 description 1
• 230000001549 tubercolostatic effect Effects 0.000 description 1