BE594946A - - Google Patents
Info
- Publication number
- BE594946A BE594946A BE594946DA BE594946A BE 594946 A BE594946 A BE 594946A BE 594946D A BE594946D A BE 594946DA BE 594946 A BE594946 A BE 594946A
- Authority
- BE
- Belgium
- Prior art keywords
- thiazole
- nitro
- furyl
- lower alkyl
- formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- ZAVLMIGIVYJYMU-UHFFFAOYSA-N 4-(5-nitrofuran-2-yl)-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2OC(=CC=2)[N+]([O-])=O)=C1 ZAVLMIGIVYJYMU-UHFFFAOYSA-N 0.000 claims description 5
- 230000000875 corresponding Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 3
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N Propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 claims description 2
- IQJVJVHMUNPANB-UHFFFAOYSA-N O1C([N+](=O)[O-])=CC=C1C1=NC=CS1 Chemical compound O1C([N+](=O)[O-])=CC=C1C1=NC=CS1 IQJVJVHMUNPANB-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000000155 melt Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- BCHLVKFPSDABRI-UHFFFAOYSA-N BrCC1=C(OC(=C1)[N+](=O)[O-])C(=O)C=1OC(=CC=1CBr)[N+](=O)[O-] Chemical compound BrCC1=C(OC(=C1)[N+](=O)[O-])C(=O)C=1OC(=CC=1CBr)[N+](=O)[O-] BCHLVKFPSDABRI-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000005712 crystallization Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- DQJAAEADFORVGZ-UHFFFAOYSA-N 2-chloro-1-(5-nitrofuran-2-yl)ethanone Chemical compound [O-][N+](=O)C1=CC=C(C(=O)CCl)O1 DQJAAEADFORVGZ-UHFFFAOYSA-N 0.000 description 1
- BGWAGUMLJYQZDM-UHFFFAOYSA-N 2-methyl-4-(5-nitrofuran-2-yl)-1,3-thiazole Chemical compound S1C(C)=NC(C=2OC(=CC=2)[N+]([O-])=O)=C1 BGWAGUMLJYQZDM-UHFFFAOYSA-N 0.000 description 1
- XTZCJUYYDYRNSR-UHFFFAOYSA-N 2-methylsulfanyl-4-(5-nitrofuran-2-yl)-1,3-thiazole Chemical compound S1C(SC)=NC(C=2OC(=CC=2)[N+]([O-])=O)=C1 XTZCJUYYDYRNSR-UHFFFAOYSA-N 0.000 description 1
- PUJLVFVPARLGGR-UHFFFAOYSA-N 4-(5-nitrofuran-2-yl)-N-phenyl-1,3-thiazol-2-amine Chemical compound O1C([N+](=O)[O-])=CC=C1C1=CSC(NC=2C=CC=CC=2)=N1 PUJLVFVPARLGGR-UHFFFAOYSA-N 0.000 description 1
- -1 5-nitro-2-furyl Chemical group 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- QHYIQVINMFTCHC-UHFFFAOYSA-N C(C)NC=1SC=C(N1)C=1OC(=CC1)[N+](=O)[O-] Chemical compound C(C)NC=1SC=C(N1)C=1OC(=CC1)[N+](=O)[O-] QHYIQVINMFTCHC-UHFFFAOYSA-N 0.000 description 1
- SLQINDZKLJRJLH-UHFFFAOYSA-N C(C)SC=1SC=C(N1)C=1OC(=CC1)[N+](=O)[O-] Chemical compound C(C)SC=1SC=C(N1)C=1OC(=CC1)[N+](=O)[O-] SLQINDZKLJRJLH-UHFFFAOYSA-N 0.000 description 1
- GMCBHCXAHXXGPQ-UHFFFAOYSA-N C(CCC)C=1SC=C(N=1)C=1OC(=CC=1)[N+](=O)[O-] Chemical compound C(CCC)C=1SC=C(N=1)C=1OC(=CC=1)[N+](=O)[O-] GMCBHCXAHXXGPQ-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- HYVVJDQGXFXBRZ-UHFFFAOYSA-N Methylcarbamodithioic acid K salt Chemical compound CNC(S)=S HYVVJDQGXFXBRZ-UHFFFAOYSA-N 0.000 description 1
- GYRMPDLIHUXUIG-UHFFFAOYSA-N N-[4-(5-Nitro-2-furyl)-2-thiazolyl]acetamide Chemical compound S1C(NC(=O)C)=NC(C=2OC(=CC=2)[N+]([O-])=O)=C1 GYRMPDLIHUXUIG-UHFFFAOYSA-N 0.000 description 1
- MIHRVCSSMAGKNH-UHFFFAOYSA-M N-ethylcarbamodithioate Chemical compound CCNC([S-])=S MIHRVCSSMAGKNH-UHFFFAOYSA-M 0.000 description 1
- BULKWIGAKJAOIE-UHFFFAOYSA-N N-methyl-4-(5-nitrofuran-2-yl)-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C=2OC(=CC=2)[N+]([O-])=O)=C1 BULKWIGAKJAOIE-UHFFFAOYSA-N 0.000 description 1
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 1
- QTBAFESXAKVFJF-UHFFFAOYSA-N OC=1SC=C(N=1)C=1OC(=CC=1)[N+](=O)[O-] Chemical compound OC=1SC=C(N=1)C=1OC(=CC=1)[N+](=O)[O-] QTBAFESXAKVFJF-UHFFFAOYSA-N 0.000 description 1
- FULZLIGZKMKICU-UHFFFAOYSA-N Phenylthiocarbamide Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 206010039447 Salmonellosis Diseases 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- KLUDQUOLAFVLOL-UHFFFAOYSA-N acetyl propanoate Chemical compound CCC(=O)OC(C)=O KLUDQUOLAFVLOL-UHFFFAOYSA-N 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000249 desinfective Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- GMEHFXXZSWDEDB-UHFFFAOYSA-N ethylthiourea Chemical compound CCNC(N)=S GMEHFXXZSWDEDB-UHFFFAOYSA-N 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000590 parasiticidal Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- WPZSAUFQHYFIPG-UHFFFAOYSA-N propanethioamide Chemical compound CCC(N)=S WPZSAUFQHYFIPG-UHFFFAOYSA-N 0.000 description 1
- ICNCMCHAPLUNBG-UHFFFAOYSA-N propyl carbamodithioate Chemical compound CCCSC(N)=S ICNCMCHAPLUNBG-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- BCFBJPKSGZNRSE-UHFFFAOYSA-N tert-butyl carbamodithioate Chemical compound CC(C)(C)SC(N)=S BCFBJPKSGZNRSE-UHFFFAOYSA-N 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE594946A true BE594946A (nl) |
Family
ID=192197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE594946D BE594946A (nl) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE594946A (nl) |
-
0
- BE BE594946D patent/BE594946A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1239933A (fr) | Polymethylene-4,5 isothiazoline-4 ones-3, leur procede de preparation et leurs utilisations comme agents bactericides et fongicides | |
| BE594946A (nl) | ||
| EP0112262A1 (fr) | Nouveaux dérivés de la benzylcarbamoylpyridine | |
| CH642614A5 (fr) | Procede de preparation d'acides trichlorophenoxyalcanoiques et de leurs derives exempts de dibenzo-p-dioxines chlorees. | |
| EP0532602B1 (fr) | Derives de benzothiazole, leur preparation et les medicaments les contenant | |
| EP0265305A1 (fr) | Nouveaux dérivés de la 5-pyrazolone, leur procédé de préparation, leur utilisation comme herbicides et les compositions les renfermant | |
| EP0408437B1 (fr) | Dérivés d'alkylimino-2 benzothiazoline, leurs procédés de préparation et les médicaments les contenant | |
| US2992225A (en) | Certain 4-(5-nitro-2-furyl)-thiazoles | |
| CA2074833A1 (fr) | Derives d'(alkylthio-3 propyl)-3 benzothiazoline, leur preparation et les medicaments les contenant | |
| CH594650A5 (en) | Antiinflammatory (1,2)-benzothiazine derivs. prepn. | |
| CH392483A (fr) | Procédé de préparation de nouveaux esters d'acides 4-halo-3-sulfamoyl-benzoïques | |
| JP2779905B2 (ja) | 工業用抗菌剤及びこれを含有した工業用抗菌剤組成物 | |
| US2733268A (en) | L-chloro-z | |
| CH655107A5 (fr) | Derives substitues de la thiamorpholine et procede pour leur preparation. | |
| BE623104A (nl) | ||
| CA2022460A1 (fr) | Derives benzothiaziniques, leur preparation et leurs applications comme medicaments ou comme intermediaires de synthese de medicaments | |
| BE552215A (nl) | ||
| US3260727A (en) | Certain aryl-substituted-1, 1-ethylenebis-lactam compounds | |
| BE589920A (nl) | ||
| BE554381A (nl) | ||
| BE541769A (nl) | ||
| BE637891A (nl) | ||
| BE520816A (nl) | ||
| JPH10120509A (ja) | 工業用抗菌剤組成物 | |
| BE662715A (nl) |