PL80863B1 - - Google Patents
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- PL80863B1 PL80863B1 PL1970138768A PL13876870A PL80863B1 PL 80863 B1 PL80863 B1 PL 80863B1 PL 1970138768 A PL1970138768 A PL 1970138768A PL 13876870 A PL13876870 A PL 13876870A PL 80863 B1 PL80863 B1 PL 80863B1
- Authority
- PL
- Poland
- Prior art keywords
- pattern
- formula
- furan
- mol
- trimethyl
- Prior art date
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- 238000000034 method Methods 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 20
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 claims description 19
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000003153 chemical reaction reagent Substances 0.000 claims description 11
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- -1 chlorocephenyl Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- HGXLVMRQQYHNGJ-UHFFFAOYSA-N 3-oxo-n-phenylpentanamide Chemical compound CCC(=O)CC(=O)NC1=CC=CC=C1 HGXLVMRQQYHNGJ-UHFFFAOYSA-N 0.000 claims 1
- WIBVNPJAIMCUJO-UHFFFAOYSA-N 4-methoxy-3-oxo-n-phenylbutanamide Chemical compound COCC(=O)CC(=O)NC1=CC=CC=C1 WIBVNPJAIMCUJO-UHFFFAOYSA-N 0.000 claims 1
- 101100231508 Caenorhabditis elegans ceh-5 gene Proteins 0.000 claims 1
- 102100038916 Caspase-5 Human genes 0.000 claims 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 claims 1
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 87
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- CFGQZVOVFIZRMN-UHFFFAOYSA-N 2-methylfuran-3-carboxylic acid Chemical compound CC=1OC=CC=1C(O)=O CFGQZVOVFIZRMN-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FDFUOWSQJFQRFG-UHFFFAOYSA-N C(CC(=O)C)(=O)O.C(C)[Na] Chemical compound C(CC(=O)C)(=O)O.C(C)[Na] FDFUOWSQJFQRFG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- BAZBYDHOWMSZBD-UHFFFAOYSA-N 2,4,5-trimethylfuran-3-carboxylic acid Chemical compound CC=1OC(C)=C(C(O)=O)C=1C BAZBYDHOWMSZBD-UHFFFAOYSA-N 0.000 description 1
- CNTHHNPBADVTRY-UHFFFAOYSA-N 2,5-dimethylfuran-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=C(C)O1 CNTHHNPBADVTRY-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- ITAIEKAUQQJLNC-UHFFFAOYSA-N 2-heptadecyl-4,5-dimethylfuran-3-carboxylic acid Chemical compound CCCCCCCCCCCCCCCCCC=1OC(C)=C(C)C=1C(O)=O ITAIEKAUQQJLNC-UHFFFAOYSA-N 0.000 description 1
- ODZTXUXIYGJLMC-UHFFFAOYSA-N 2-hydroxycyclohexan-1-one Chemical compound OC1CCCCC1=O ODZTXUXIYGJLMC-UHFFFAOYSA-N 0.000 description 1
- OIMRLHCSLQUXLL-UHFFFAOYSA-N 3-chlorobutan-2-one Chemical compound CC(Cl)C(C)=O OIMRLHCSLQUXLL-UHFFFAOYSA-N 0.000 description 1
- IHCCAYCGZOLTEU-UHFFFAOYSA-M 3-furoate Chemical compound [O-]C(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-M 0.000 description 1
- XRZDIHADHZSFBB-UHFFFAOYSA-N 3-oxo-n,3-diphenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)C1=CC=CC=C1 XRZDIHADHZSFBB-UHFFFAOYSA-N 0.000 description 1
- VCCNAPAOKUSZGC-UHFFFAOYSA-N 3-oxo-n-(2-phenylphenyl)butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C1=CC=CC=C1 VCCNAPAOKUSZGC-UHFFFAOYSA-N 0.000 description 1
- BVEYJWQCMOVMAR-UHFFFAOYSA-N 5-Hydroxy-4-octanone Chemical compound CCCC(O)C(=O)CCC BVEYJWQCMOVMAR-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FGOFNVXHDGQVBG-UHFFFAOYSA-N N-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1NC(C)=O FGOFNVXHDGQVBG-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000001649 bromium compounds Chemical group 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940120503 dihydroxyacetone Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- DOHUEYINVDLUSG-UHFFFAOYSA-N ethyl 2-methylfuran-3-carboxylate Chemical compound CCOC(=O)C=1C=COC=1C DOHUEYINVDLUSG-UHFFFAOYSA-N 0.000 description 1
- ZSZUZHXUJXYSMM-UHFFFAOYSA-N ethyl 3-oxoicosanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)CC(=O)OCC ZSZUZHXUJXYSMM-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KYYRTDXOHQYZPO-UHFFFAOYSA-N n-(2-methoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC=CC=C1NC(=O)CC(C)=O KYYRTDXOHQYZPO-UHFFFAOYSA-N 0.000 description 1
- PCGMZJHAOYYUHF-UHFFFAOYSA-N n-(4-fluorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=C(F)C=C1 PCGMZJHAOYYUHF-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79910969A | 1969-02-13 | 1969-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL80863B1 true PL80863B1 (en, 2012) | 1975-08-30 |
Family
ID=25175061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970138768A PL80863B1 (en, 2012) | 1969-02-13 | 1970-02-12 |
Country Status (20)
| Country | Link |
|---|---|
| AT (1) | AT294060B (en, 2012) |
| BE (1) | BE745863A (en, 2012) |
| CA (1) | CA932334A (en, 2012) |
| CH (2) | CH558349A (en, 2012) |
| CS (1) | CS188869B2 (en, 2012) |
| DE (1) | DE2006472C2 (en, 2012) |
| DK (1) | DK134176B (en, 2012) |
| EG (1) | EG12357A (en, 2012) |
| ES (1) | ES376539A1 (en, 2012) |
| FR (1) | FR2068181A5 (en, 2012) |
| GB (1) | GB1303844A (en, 2012) |
| IL (1) | IL33880A (en, 2012) |
| LU (1) | LU60345A1 (en, 2012) |
| NL (1) | NL172061C (en, 2012) |
| NO (1) | NO134337C (en, 2012) |
| PL (1) | PL80863B1 (en, 2012) |
| RO (1) | RO57890A (en, 2012) |
| SE (1) | SE393985C (en, 2012) |
| TR (1) | TR16671A (en, 2012) |
| ZA (1) | ZA70828B (en, 2012) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3959481A (en) * | 1969-02-13 | 1976-05-25 | Uniroyal | Method of protecting plants from fungal diseases using furan-3-carboxamide derivatives |
| DE2019535C3 (de) * | 1970-04-23 | 1987-02-12 | Basf Ag, 6700 Ludwigshafen | 2,5-Dimethyl-furan-3-carbonsäure-cyclohexylamid und diese Verbindung enthaltende fungizide Mittel |
| BE795524A (fr) * | 1972-02-16 | 1973-08-16 | Basf Ag | Procede de preparation d'esters de l'acide dimethyl-2,5-furanne-carboxylique-3 |
| GB1387652A (en) * | 1972-05-10 | 1975-03-19 | Shell Int Research | Process for preparing furan carboxamides |
| DE2703023A1 (de) * | 1977-01-26 | 1978-07-27 | Basf Ag | Furanderivate |
| DE2800505A1 (de) | 1978-01-05 | 1979-07-19 | Consortium Elektrochem Ind | Verfahren zur herstellung von substituierten furanen |
| DE2826013A1 (de) * | 1978-06-14 | 1980-01-03 | Basf Ag | Verfahren zur herstellung von 2,5-dimethylfuran-3-carbonsaeurealkylestern |
| DE10222884A1 (de) | 2002-05-23 | 2003-12-04 | Bayer Cropscience Ag | Furancarboxamide |
| US20050113566A1 (en) * | 2003-04-25 | 2005-05-26 | Player Mark R. | Inhibitors of C-FMS kinase |
| DE102004005785A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | 2-Halogenfuryl/thienyl-3-carboxamide |
| DE102004005787A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Carboxamide |
| DE102004005786A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Haloalkylcarboxamide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1215066A (en) * | 1968-03-25 | 1970-12-09 | Shell Int Research | Acrylamides and their use as fungicides |
| DE1768686B1 (de) * | 1968-06-19 | 1971-05-27 | Basf Ag | Furan-3-carbonsaeureanilide und deren Verwendung als Fungizid |
-
1969
- 1969-10-28 CA CA066031A patent/CA932334A/en not_active Expired
-
1970
- 1970-02-06 ZA ZA700828A patent/ZA70828B/xx unknown
- 1970-02-09 GB GB608370A patent/GB1303844A/en not_active Expired
- 1970-02-10 IL IL33880A patent/IL33880A/xx unknown
- 1970-02-11 SE SE7001749A patent/SE393985C/xx unknown
- 1970-02-12 DK DK68870AA patent/DK134176B/da unknown
- 1970-02-12 DE DE2006472A patent/DE2006472C2/de not_active Expired
- 1970-02-12 NO NO495/70A patent/NO134337C/no unknown
- 1970-02-12 PL PL1970138768A patent/PL80863B1/pl unknown
- 1970-02-12 CS CS70991A patent/CS188869B2/cs unknown
- 1970-02-12 BE BE745863D patent/BE745863A/xx not_active IP Right Cessation
- 1970-02-12 FR FR7005054A patent/FR2068181A5/fr not_active Expired
- 1970-02-12 NL NLAANVRAGE7002030,A patent/NL172061C/xx not_active IP Right Cessation
- 1970-02-13 LU LU60345D patent/LU60345A1/xx unknown
- 1970-02-13 CH CH211370A patent/CH558349A/xx not_active IP Right Cessation
- 1970-02-13 AT AT133670A patent/AT294060B/de not_active IP Right Cessation
- 1970-02-13 ES ES376539A patent/ES376539A1/es not_active Expired
- 1970-02-13 RO RO62460A patent/RO57890A/ro unknown
- 1970-02-13 TR TR16671A patent/TR16671A/xx unknown
- 1970-02-13 CH CH1666673A patent/CH567495A5/xx not_active IP Right Cessation
-
1976
- 1976-09-04 EG EG547/76A patent/EG12357A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| SE393985B (sv) | 1977-05-31 |
| TR16671A (tr) | 1973-03-01 |
| NL172061C (nl) | 1983-07-01 |
| GB1303844A (en, 2012) | 1973-01-24 |
| NL172061B (nl) | 1983-02-01 |
| CH567495A5 (en, 2012) | 1975-10-15 |
| IL33880A0 (en) | 1970-04-20 |
| LU60345A1 (en, 2012) | 1971-06-21 |
| DK134176B (da) | 1976-09-27 |
| NL7002030A (en, 2012) | 1970-08-17 |
| CA932334A (en) | 1973-08-21 |
| BE745863A (fr) | 1970-08-12 |
| CH558349A (de) | 1975-01-31 |
| FR2068181A5 (en, 2012) | 1971-08-20 |
| ZA70828B (en) | 1971-09-29 |
| CS188869B2 (en) | 1979-03-30 |
| ES376539A1 (es) | 1972-04-16 |
| EG12357A (en) | 1978-09-30 |
| RO57890A (en, 2012) | 1975-08-15 |
| NO134337C (en, 2012) | 1976-09-22 |
| AT294060B (de) | 1971-11-10 |
| DE2006472C2 (de) | 1983-12-22 |
| DK134176C (en, 2012) | 1977-02-28 |
| NO134337B (en, 2012) | 1976-06-14 |
| IL33880A (en) | 1984-09-30 |
| SE393985C (sv) | 1980-12-22 |
| DE2006472A1 (de) | 1970-08-27 |
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