BE490386A - - Google Patents
Info
- Publication number
- BE490386A BE490386A BE490386DA BE490386A BE 490386 A BE490386 A BE 490386A BE 490386D A BE490386D A BE 490386DA BE 490386 A BE490386 A BE 490386A
- Authority
- BE
- Belgium
- Prior art keywords
- chlorphenyl
- ethyl
- parts
- isopropyl
- prepared
- Prior art date
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 150000004283 biguanides Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000003009 desulfurizing Effects 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000006477 desulfuration reaction Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 1
- 238000002844 melting Methods 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UKWHYYKOEPRTIC-UHFFFAOYSA-N Mercury(II) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 6
- MZZVFXMTZTVUFO-UHFFFAOYSA-N 1-chloro-4-isothiocyanatobenzene Chemical compound ClC1=CC=C(N=C=S)C=C1 MZZVFXMTZTVUFO-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- YGIZYFWSENWXPK-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(propan-2-ylcarbamothioyl)thiourea Chemical compound CC(C)NC(=S)NC(=S)NC1=CC=C(Cl)C=C1 YGIZYFWSENWXPK-UHFFFAOYSA-N 0.000 description 4
- HMDYXMGGYFYARX-UHFFFAOYSA-N Br.C(C)SC(NC(C)C)=N Chemical compound Br.C(C)SC(NC(C)C)=N HMDYXMGGYFYARX-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic Effects 0.000 description 4
- 229940101209 mercuric oxide Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000002829 nitrogen Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003463 sulfur Chemical class 0.000 description 3
- 241000208818 Helianthus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- FAPXKQMFIRYKMF-UHFFFAOYSA-N 1-(diaminomethylidene)-2-propylguanidine Chemical compound CCCN=C(N)N=C(N)N FAPXKQMFIRYKMF-UHFFFAOYSA-N 0.000 description 1
- SARMGXPVOFNNNG-UHFFFAOYSA-N 1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine;hydron;chloride Chemical compound Cl.CC(C)N=C(N)N=C(N)NC1=CC=C(Cl)C=C1 SARMGXPVOFNNNG-UHFFFAOYSA-N 0.000 description 1
- WGXCKFMVBAOIFH-UHFFFAOYSA-N 1-chloro-3-isothiocyanatobenzene Chemical compound ClC1=CC=CC(N=C=S)=C1 WGXCKFMVBAOIFH-UHFFFAOYSA-N 0.000 description 1
- SNLGBRZZFRSXHA-UHFFFAOYSA-N 1-iodo-4-isothiocyanatobenzene Chemical compound IC1=CC=C(N=C=S)C=C1 SNLGBRZZFRSXHA-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-Ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- ZZUOUWSZGDWNPI-UHFFFAOYSA-N Br.C(CC)NC(SCC)=N Chemical compound Br.C(CC)NC(SCC)=N ZZUOUWSZGDWNPI-UHFFFAOYSA-N 0.000 description 1
- VPDHAXJCIUUBKV-UHFFFAOYSA-N BrC1=CC=C(C=C1)NC(=S)NC(=S)NC(C)C Chemical compound BrC1=CC=C(C=C1)NC(=S)NC(=S)NC(C)C VPDHAXJCIUUBKV-UHFFFAOYSA-N 0.000 description 1
- YXSDXJWURJSEHU-UHFFFAOYSA-N Cl.ClC1=CC=C(C=C1)NC(=N)NC(=N)NCCCC Chemical compound Cl.ClC1=CC=C(C=C1)NC(=N)NC(=N)NCCCC YXSDXJWURJSEHU-UHFFFAOYSA-N 0.000 description 1
- MVKAUBFZVCHYCN-UHFFFAOYSA-N Cl.IC1=CC=C(C=C1)NC(=N)NC(=N)NC(C)C Chemical compound Cl.IC1=CC=C(C=C1)NC(=N)NC(=N)NC(C)C MVKAUBFZVCHYCN-UHFFFAOYSA-N 0.000 description 1
- ODGHADRVONHNQC-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC(=S)NC(=S)NCC Chemical compound ClC1=CC=C(C=C1)NC(=S)NC(=S)NCC ODGHADRVONHNQC-UHFFFAOYSA-N 0.000 description 1
- PLLUJWHIOUVEHY-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC(=S)NC(=S)NCCC Chemical compound ClC1=CC=C(C=C1)NC(=S)NC(=S)NCCC PLLUJWHIOUVEHY-UHFFFAOYSA-N 0.000 description 1
- SZBXCCVBCOJBMY-UHFFFAOYSA-N IC1=CC=C(C=C1)NC(=S)NC(=S)NC(C)C Chemical compound IC1=CC=C(C=C1)NC(=S)NC(=S)NC(C)C SZBXCCVBCOJBMY-UHFFFAOYSA-N 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M Sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- GMZHWOAPIKGZAJ-UHFFFAOYSA-N [N'-[N'-(4-chlorophenyl)carbamimidoyl]carbamimidoyl]-propan-2-ylazanium;acetate Chemical compound CC([O-])=O.CC(C)[NH2+]\C(N)=N\C(N)=NC1=CC=C(Cl)C=C1 GMZHWOAPIKGZAJ-UHFFFAOYSA-N 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000000078 anti-malarial Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SANOEYUUMMQDEW-UHFFFAOYSA-N ethyl N'-butylcarbamimidothioate;hydrobromide Chemical compound Br.CCCCNC(=N)SCC SANOEYUUMMQDEW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- -1 melting at 129 C Chemical compound 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004434 sulfur atoms Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE490386A true BE490386A (xx) |
Family
ID=135108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE490386D BE490386A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE490386A (xx) |
-
0
- BE BE490386D patent/BE490386A/fr unknown
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