SU610490A3 - Способ получени производных оксазола - Google Patents
Способ получени производных оксазолаInfo
- Publication number
- SU610490A3 SU610490A3 SU762367752A SU2367752A SU610490A3 SU 610490 A3 SU610490 A3 SU 610490A3 SU 762367752 A SU762367752 A SU 762367752A SU 2367752 A SU2367752 A SU 2367752A SU 610490 A3 SU610490 A3 SU 610490A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- methyloxazole
- butyl
- kip
- alkyl
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000007978 oxazole derivatives Chemical class 0.000 title claims description 4
- -1 (2-Methylbutyl) -propionamide-d-methyloxazole Chemical compound 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl 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
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000003951 lactams Chemical group 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229940047889 isobutyramide Drugs 0.000 claims 2
- YGESXXJIWIMYBD-UHFFFAOYSA-N 2-cyclohexylbutanamide Chemical compound CCC(C(N)=O)C1CCCCC1 YGESXXJIWIMYBD-UHFFFAOYSA-N 0.000 claims 1
- ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 2-methyl-1,3-oxazole Chemical compound CC1=NC=CO1 ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- 238000002474 experimental method Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- PEFMXZJRCDFXFU-UHFFFAOYSA-N n-benzylpentanamide Chemical compound CCCCC(=O)NCC1=CC=CC=C1 PEFMXZJRCDFXFU-UHFFFAOYSA-N 0.000 claims 1
- QAIVBMMCFLHXCN-UHFFFAOYSA-N n-butyl-2-methylbutanamide Chemical compound CCCCNC(=O)C(C)CC QAIVBMMCFLHXCN-UHFFFAOYSA-N 0.000 claims 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 239000007788 liquid Substances 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000004821 distillation Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- GZAROOOHRGKEPC-UHFFFAOYSA-N n-butyl-2-methylpropanamide Chemical compound CCCCNC(=O)C(C)C GZAROOOHRGKEPC-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 2
- ZFAIQINIVNSNQE-UHFFFAOYSA-N 2-butylsulfinyl-4-methyl-1,3-oxazole Chemical compound CCCCS(=O)C1=NC(C)=CO1 ZFAIQINIVNSNQE-UHFFFAOYSA-N 0.000 description 2
- RQAIEHDXUZPMBJ-UHFFFAOYSA-N 2-chloro-5-phenyl-1,3-oxazole Chemical compound O1C(Cl)=NC=C1C1=CC=CC=C1 RQAIEHDXUZPMBJ-UHFFFAOYSA-N 0.000 description 2
- DQWFXAYJAOLPDI-UHFFFAOYSA-N 2-cyclohexylsulfinyl-4-methyl-1,3-oxazole Chemical compound CC1=COC(S(=O)C2CCCCC2)=N1 DQWFXAYJAOLPDI-UHFFFAOYSA-N 0.000 description 2
- WAXRUMDVEFKCBB-UHFFFAOYSA-N 2-ethylsulfinyl-1,3-oxazole Chemical compound CCS(=O)C1=NC=CO1 WAXRUMDVEFKCBB-UHFFFAOYSA-N 0.000 description 2
- SCFCQBPUOMKUGV-UHFFFAOYSA-N 2-hexylsulfinyl-4-methyl-1,3-oxazole Chemical compound CCCCCCS(=O)C1=NC(C)=CO1 SCFCQBPUOMKUGV-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- GQRJYPGJHFIZOB-UHFFFAOYSA-N 5-methyl-2-methylsulfinyl-1,3-oxazole Chemical compound CC1=CN=C(S(C)=O)O1 GQRJYPGJHFIZOB-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- QCYFOZWGXKXDJA-UHFFFAOYSA-N 1-butoxyhexane Chemical compound CCCCCCOCCCC QCYFOZWGXKXDJA-UHFFFAOYSA-N 0.000 description 1
- YTGDJSCRTHJOSE-UHFFFAOYSA-N 2-(benzenesulfonyl)-4,5-diphenyl-1,3-oxazole Chemical compound C=1C=CC=CC=1S(=O)(=O)C(O1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 YTGDJSCRTHJOSE-UHFFFAOYSA-N 0.000 description 1
- OEANAPSFXQOCFL-UHFFFAOYSA-N 2-benzylsulfinyl-4-methyl-1,3-oxazole Chemical compound CC1=COC(S(=O)CC=2C=CC=CC=2)=N1 OEANAPSFXQOCFL-UHFFFAOYSA-N 0.000 description 1
- FIVZZSQNOFRFCO-UHFFFAOYSA-N 2-butylsulfanyl-4-methyl-1,3-oxazole Chemical compound CCCCSC1=NC(C)=CO1 FIVZZSQNOFRFCO-UHFFFAOYSA-N 0.000 description 1
- SHDAQHZKUROXEE-UHFFFAOYSA-N 2-cyclohexylsulfanyl-4-methyl-1,3-oxazole Chemical compound CC1=COC(SC2CCCCC2)=N1 SHDAQHZKUROXEE-UHFFFAOYSA-N 0.000 description 1
- KCOVPCFVNYUBAL-UHFFFAOYSA-N 2-hexylsulfanyl-4-methyl-1,3-oxazole Chemical compound CCCCCCSC1=NC(C)=CO1 KCOVPCFVNYUBAL-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- VFPNPBIRNHKULU-UHFFFAOYSA-N 3-butyl-4-methoxy-N-(4-methyl-1,3-oxazol-2-yl)benzamide Chemical compound C(CCC)C=1C=C(C(=O)NC=2OC=C(N=2)C)C=CC=1OC VFPNPBIRNHKULU-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
- YVORRVFKHZLJGZ-UHFFFAOYSA-N 4,5-Dimethyloxazole Chemical compound CC=1N=COC=1C YVORRVFKHZLJGZ-UHFFFAOYSA-N 0.000 description 1
- TWAYCFHPZZAERR-UHFFFAOYSA-N 4,5-dimethyl-2-methylsulfonyl-1,3-oxazole Chemical compound CC=1N=C(S(C)(=O)=O)OC=1C TWAYCFHPZZAERR-UHFFFAOYSA-N 0.000 description 1
- NOXOKDZRWNZBPP-UHFFFAOYSA-N 4-ethyl-2-methylsulfinyl-1,3-oxazole Chemical compound CCC1=COC(S(C)=O)=N1 NOXOKDZRWNZBPP-UHFFFAOYSA-N 0.000 description 1
- DBYQGTLFSQKPCA-UHFFFAOYSA-N 4-hydroxy-5-methyl-2-propylfuran-3-one Chemical compound CCCC1OC(C)=C(O)C1=O DBYQGTLFSQKPCA-UHFFFAOYSA-N 0.000 description 1
- ONKNTGBPBLBZFN-UHFFFAOYSA-N 4-methyl-2-methylsulfinyl-1,3-oxazole Chemical compound CC1=COC(S(C)=O)=N1 ONKNTGBPBLBZFN-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- SZMNDOUFZGODBR-UHFFFAOYSA-N decan-5-ol Chemical compound CCCCCC(O)CCCC SZMNDOUFZGODBR-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ICRWBBQXMVAKAK-UHFFFAOYSA-N n,2-dimethyl-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound CC(C)C(=O)N(C)C1=NC(C)=CO1 ICRWBBQXMVAKAK-UHFFFAOYSA-N 0.000 description 1
- UYGVTFVGFQHCDZ-UHFFFAOYSA-N n-butan-2-yl-2-methylpropanamide Chemical compound CCC(C)NC(=O)C(C)C UYGVTFVGFQHCDZ-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OJPLOCHZOYBEIG-UHFFFAOYSA-N n-butyl-2-ethyl-n-(4-methyl-1,3-oxazol-2-yl)butanamide Chemical compound CCCCN(C(=O)C(CC)CC)C1=NC(C)=CO1 OJPLOCHZOYBEIG-UHFFFAOYSA-N 0.000 description 1
- BXGIGCLJUGBLPJ-UHFFFAOYSA-N n-butyl-2-methyl-n-(1,3-oxazol-2-yl)propanamide Chemical compound CCCCN(C(=O)C(C)C)C1=NC=CO1 BXGIGCLJUGBLPJ-UHFFFAOYSA-N 0.000 description 1
- ONAIAWZYXZWAKG-UHFFFAOYSA-N n-butyl-2-methyl-n-(5-phenyl-1,3-oxazol-2-yl)propanamide Chemical compound O1C(N(C(=O)C(C)C)CCCC)=NC=C1C1=CC=CC=C1 ONAIAWZYXZWAKG-UHFFFAOYSA-N 0.000 description 1
- HFMVLLSXUNYXLP-UHFFFAOYSA-N n-butyl-4-methyl-n-(4-methyl-1,3-oxazol-2-yl)benzamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1=CC=C(C)C=C1 HFMVLLSXUNYXLP-UHFFFAOYSA-N 0.000 description 1
- KWPMZNUVHZKWIT-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)-3-(trifluoromethyl)benzamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1=CC=CC(C(F)(F)F)=C1 KWPMZNUVHZKWIT-UHFFFAOYSA-N 0.000 description 1
- BSMLJQAAMZFOMA-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)-3-phenylpropanamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)CCC1=CC=CC=C1 BSMLJQAAMZFOMA-UHFFFAOYSA-N 0.000 description 1
- WLEYNUMIDNFBGK-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)-4-nitrobenzamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1=CC=C([N+]([O-])=O)C=C1 WLEYNUMIDNFBGK-UHFFFAOYSA-N 0.000 description 1
- DUZJWTFIQCWMSD-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)cycloheptanecarboxamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1CCCCCC1 DUZJWTFIQCWMSD-UHFFFAOYSA-N 0.000 description 1
- SHPIALGSGCJLNJ-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)cyclohexanecarboxamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1CCCCC1 SHPIALGSGCJLNJ-UHFFFAOYSA-N 0.000 description 1
- YSKPHODLBKBYJO-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)cyclopropanecarboxamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1CC1 YSKPHODLBKBYJO-UHFFFAOYSA-N 0.000 description 1
- VOXDEQVFCVFBEM-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)pentanamide Chemical compound CCCCC(=O)N(CCCC)C1=NC(C)=CO1 VOXDEQVFCVFBEM-UHFFFAOYSA-N 0.000 description 1
- PKOPLDUHARSIKV-UHFFFAOYSA-N n-butylpentanamide Chemical compound CCCCNC(=O)CCCC PKOPLDUHARSIKV-UHFFFAOYSA-N 0.000 description 1
- XQZDWKBCGAJXLC-UHFFFAOYSA-N n-butylpropanamide Chemical compound CCCCNC(=O)CC XQZDWKBCGAJXLC-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- KJVRLFWTIGWXFK-UHFFFAOYSA-N n-prop-2-enylbenzamide Chemical compound C=CCNC(=O)C1=CC=CC=C1 KJVRLFWTIGWXFK-UHFFFAOYSA-N 0.000 description 1
- KTJYOKLCBAFHDD-UHFFFAOYSA-N n-prop-2-enylbutanamide Chemical compound CCCC(=O)NCC=C KTJYOKLCBAFHDD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- PZHNNJXWQYFUTD-UHFFFAOYSA-N phosphorus triiodide Chemical compound IP(I)I PZHNNJXWQYFUTD-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings 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
- C07D263/46—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings 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
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24552/75A GB1552125A (en) | 1975-06-07 | 1975-06-07 | 2-acylamino oxazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU610490A3 true SU610490A3 (ru) | 1978-06-05 |
Family
ID=10213418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762367752A SU610490A3 (ru) | 1975-06-07 | 1976-06-07 | Способ получени производных оксазола |
Country Status (30)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH655312A5 (de) * | 1982-02-09 | 1986-04-15 | Sandoz Ag | Chloracetamide. |
| PL372332A1 (pl) | 2005-01-19 | 2006-07-24 | ADAMED Sp.z o.o. | Nowe związki, pochodne kwasu 3-fenylopropionowego |
| EP2112143A1 (de) | 2008-04-22 | 2009-10-28 | Bayer CropScience AG | 2-(Benzylsulfonyl)-Oxazol-Derivate, chirale 2-(Benzylsulfinyl)-Oxazol-Derivate 2-(Benzylsulfanyl-Oxazol Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| EP2112149A1 (de) | 2008-04-22 | 2009-10-28 | Bayer CropScience Aktiengesellschaft | 2-[(1h-Pyrazol-4-ylmethyl)-sulfonyl]-Oxazol-Derivate, 2-[(1H-Pyrazol-4-ylmethyl)-sulfanyl]-Oxazol-Derivate und chirale 2-[(1H-Pyrazol-4-ylmethyl)-sulfinyl]-Oxazol-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1497536A (en) * | 1973-12-17 | 1978-01-12 | Lilly Industries Ltd | 2-acylaminooxazoles methods for their preparation and their use |
| US3888870A (en) * | 1974-03-08 | 1975-06-10 | Sandoz Ag | 2-sulfinyl-thiazoles and oxazoles |
-
1975
- 1975-06-07 GB GB24552/75A patent/GB1552125A/en not_active Expired
-
1976
- 1976-06-01 CA CA253,867A patent/CA1080707A/en not_active Expired
- 1976-06-01 GR GR50869A patent/GR60337B/el unknown
- 1976-06-01 NZ NZ181026A patent/NZ181026A/xx unknown
- 1976-06-02 AR AR263482A patent/AR219281A1/es active
- 1976-06-02 DK DK243376A patent/DK243376A/da not_active Application Discontinuation
- 1976-06-02 IE IE1181/76A patent/IE43314B1/en unknown
- 1976-06-02 SE SE7606227A patent/SE7606227L/xx not_active Application Discontinuation
- 1976-06-03 YU YU01369/76A patent/YU136976A/xx unknown
- 1976-06-03 PT PT65183A patent/PT65183B/pt unknown
- 1976-06-03 AU AU14616/76A patent/AU502416B2/en not_active Expired
- 1976-06-03 BE BE6045540A patent/BE842580A/xx not_active IP Right Cessation
- 1976-06-03 HU HU76LI295A patent/HU174777B/hu unknown
- 1976-06-03 IL IL49710A patent/IL49710A/xx unknown
- 1976-06-04 JP JP51066028A patent/JPS51146462A/ja active Pending
- 1976-06-04 DD DD193193A patent/DD125347A6/xx unknown
- 1976-06-04 ZA ZA763336A patent/ZA763336B/xx unknown
- 1976-06-04 DE DE19762625229 patent/DE2625229A1/de not_active Withdrawn
- 1976-06-04 PL PL1976190128A patent/PL100004B1/pl unknown
- 1976-06-04 FR FR7616975A patent/FR2313372A1/fr active Granted
- 1976-06-04 CH CH710576A patent/CH598236A5/xx not_active IP Right Cessation
- 1976-06-04 AT AT412576A patent/AT345278B/de not_active IP Right Cessation
- 1976-06-04 ES ES448591A patent/ES448591A1/es not_active Expired
- 1976-06-04 PH PH18534A patent/PH14307A/en unknown
- 1976-06-05 RO RO7686351A patent/RO69114A/ro unknown
- 1976-06-07 SU SU762367752A patent/SU610490A3/ru active
- 1976-06-07 MX MX000274U patent/MX3140E/es unknown
- 1976-06-07 CS CS763747A patent/CS190536B2/cs unknown
- 1976-06-07 BG BG033393A patent/BG25516A3/xx unknown
- 1976-06-08 NL NL7606177A patent/NL7606177A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DD125347A6 (de) | 1977-04-13 |
| SE7606227L (sv) | 1976-11-08 |
| MX3140E (es) | 1980-05-06 |
| GB1552125A (en) | 1979-09-05 |
| AU502416B2 (en) | 1979-07-26 |
| BE842580A (fr) | 1976-12-03 |
| ZA763336B (en) | 1977-05-25 |
| IE43314L (en) | 1976-12-07 |
| CA1080707A (en) | 1980-07-01 |
| NZ181026A (en) | 1978-06-20 |
| PT65183B (en) | 1978-11-06 |
| RO69114A (ro) | 1980-08-15 |
| PL100004B1 (pl) | 1978-08-31 |
| FR2313372B1 (cg-RX-API-DMAC10.html) | 1980-02-15 |
| FR2313372A1 (fr) | 1976-12-31 |
| ATA412576A (de) | 1978-01-15 |
| PH14307A (en) | 1981-05-19 |
| AU1461676A (en) | 1977-12-08 |
| AT345278B (de) | 1978-09-11 |
| IL49710A0 (en) | 1976-08-31 |
| GR60337B (en) | 1978-05-15 |
| DK243376A (da) | 1976-12-08 |
| DE2625229A1 (de) | 1976-12-23 |
| CS190536B2 (en) | 1979-05-31 |
| AR219281A1 (es) | 1980-08-15 |
| ES448591A1 (es) | 1977-07-16 |
| IE43314B1 (en) | 1981-01-28 |
| NL7606177A (nl) | 1976-12-09 |
| YU136976A (en) | 1983-02-28 |
| PT65183A (en) | 1976-07-01 |
| HU174777B (hu) | 1980-03-28 |
| BG25516A3 (en) | 1978-10-10 |
| JPS51146462A (en) | 1976-12-16 |
| IL49710A (en) | 1979-03-12 |
| CH598236A5 (cg-RX-API-DMAC10.html) | 1978-04-28 |
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