DE2625229A1 - Verfahren zur herstellung von oxazolderivaten und oxazolderivate - Google Patents
Verfahren zur herstellung von oxazolderivaten und oxazolderivateInfo
- Publication number
- DE2625229A1 DE2625229A1 DE19762625229 DE2625229A DE2625229A1 DE 2625229 A1 DE2625229 A1 DE 2625229A1 DE 19762625229 DE19762625229 DE 19762625229 DE 2625229 A DE2625229 A DE 2625229A DE 2625229 A1 DE2625229 A1 DE 2625229A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- methyloxazole
- cycloalkyl
- phenyl
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 16
- 150000007978 oxazole derivatives Chemical class 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- -1 substituted Chemical class 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 150000003951 lactams Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000009835 boiling Methods 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 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 14
- 238000004458 analytical method Methods 0.000 description 11
- 239000012230 colorless oil Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 7
- 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
- 238000004821 distillation Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 239000004533 oil dispersion Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YVORRVFKHZLJGZ-UHFFFAOYSA-N 4,5-Dimethyloxazole Chemical compound CC=1N=COC=1C YVORRVFKHZLJGZ-UHFFFAOYSA-N 0.000 description 3
- ONKNTGBPBLBZFN-UHFFFAOYSA-N 4-methyl-2-methylsulfinyl-1,3-oxazole Chemical compound CC1=COC(S(C)=O)=N1 ONKNTGBPBLBZFN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 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
- 150000002916 oxazoles Chemical class 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- QCYFOZWGXKXDJA-UHFFFAOYSA-N 1-butoxyhexane Chemical compound CCCCCCOCCCC QCYFOZWGXKXDJA-UHFFFAOYSA-N 0.000 description 2
- 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 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
- XYLFVYPPRKQXKJ-UHFFFAOYSA-N 4,5-dimethyl-2-methylsulfanyl-1,3-oxazole Chemical compound CSC1=NC(C)=C(C)O1 XYLFVYPPRKQXKJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FKWZXMKIWPHHMD-UHFFFAOYSA-N 4-methyl-2-methylsulfanyl-1,3-oxazole Chemical compound CSC1=NC(C)=CO1 FKWZXMKIWPHHMD-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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- LASKOYXOOOTXQS-UHFFFAOYSA-N n-butan-2-yl-2-methyl-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound CCC(C)N(C(=O)C(C)C)C1=NC(C)=CO1 LASKOYXOOOTXQS-UHFFFAOYSA-N 0.000 description 2
- JFCMWZKQUUZFLN-UHFFFAOYSA-N n-butan-2-yl-n-(4-methyl-1,3-oxazol-2-yl)butanamide Chemical compound CCCC(=O)N(C(C)CC)C1=NC(C)=CO1 JFCMWZKQUUZFLN-UHFFFAOYSA-N 0.000 description 2
- XSBXJNYUXNMUOK-UHFFFAOYSA-N n-butyl-2-methyl-n-(4-methyl-1,3-oxazol-2-yl)butanamide Chemical compound CCCCN(C(=O)C(C)CC)C1=NC(C)=CO1 XSBXJNYUXNMUOK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- ONXLZGFECOWEGI-UHFFFAOYSA-N 1-(4-methyl-1,3-oxazol-2-yl)azepan-2-one Chemical compound CC1=COC(N2C(CCCCC2)=O)=N1 ONXLZGFECOWEGI-UHFFFAOYSA-N 0.000 description 1
- BNZQGRBBUHRDHJ-UHFFFAOYSA-N 2,2-dimethylhexanamide Chemical compound CCCCC(C)(C)C(N)=O BNZQGRBBUHRDHJ-UHFFFAOYSA-N 0.000 description 1
- CNNNJMWLGUNYCF-UHFFFAOYSA-N 2-(benzenesulfinyl)-4,5-diphenyl-1,3-oxazole Chemical compound C=1C=CC=CC=1S(=O)C(O1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CNNNJMWLGUNYCF-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
- ILHKKKZBJFJGHE-UHFFFAOYSA-N 2-benzylsulfanyl-4-methyl-1,3-oxazole Chemical compound CC1=COC(SCC=2C=CC=CC=2)=N1 ILHKKKZBJFJGHE-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
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-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
- SOAZJBLSEVXTCZ-UHFFFAOYSA-N 2-ethyl-n-(2-methoxyethyl)-n-(4-methyl-1,3-oxazol-2-yl)butanamide Chemical compound CCC(CC)C(=O)N(CCOC)C1=NC(C)=CO1 SOAZJBLSEVXTCZ-UHFFFAOYSA-N 0.000 description 1
- RBUAVAWCIPJZIP-UHFFFAOYSA-N 2-ethylsulfanyl-1,3-oxazole Chemical compound CCSC1=NC=CO1 RBUAVAWCIPJZIP-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
- WBPNQQLVXYWYLO-UHFFFAOYSA-N 2-iodo-4,5-diphenyl-1,3-oxazole Chemical compound O1C(I)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 WBPNQQLVXYWYLO-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
- LAXDZLSWPAFVGM-UHFFFAOYSA-N 2-methyl-n-(2-methylbutyl)-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound CCC(C)CN(C(=O)C(C)C)C1=NC(C)=CO1 LAXDZLSWPAFVGM-UHFFFAOYSA-N 0.000 description 1
- PFOHISWVBXEJLZ-UHFFFAOYSA-N 2-methyl-n-(4-methyl-1,3-oxazol-2-yl)-n-[(3-methylphenyl)methyl]propanamide Chemical compound N=1C(C)=COC=1N(C(=O)C(C)C)CC1=CC=CC(C)=C1 PFOHISWVBXEJLZ-UHFFFAOYSA-N 0.000 description 1
- WBFPJYGEGCAWKY-UHFFFAOYSA-N 2-methyl-n-(4-methyl-1,3-oxazol-2-yl)-n-[(4-methylphenyl)methyl]propanamide Chemical compound N=1C(C)=COC=1N(C(=O)C(C)C)CC1=CC=C(C)C=C1 WBFPJYGEGCAWKY-UHFFFAOYSA-N 0.000 description 1
- SKRBDQGRMHOMSE-UHFFFAOYSA-N 2-methyl-n-(4-methyl-1,3-oxazol-2-yl)-n-pentylpropanamide Chemical compound CCCCCN(C(=O)C(C)C)C1=NC(C)=CO1 SKRBDQGRMHOMSE-UHFFFAOYSA-N 0.000 description 1
- KBCICOXIBJQUHH-UHFFFAOYSA-N 2-methyl-n-(4-methyl-1,3-oxazol-2-yl)-n-propan-2-ylpropanamide Chemical compound CC(C)C(=O)N(C(C)C)C1=NC(C)=CO1 KBCICOXIBJQUHH-UHFFFAOYSA-N 0.000 description 1
- RNOKFJMXGUXDFP-UHFFFAOYSA-N 2-methylsulfinyl-4-phenyl-1,3-oxazole Chemical compound O1C(S(=O)C)=NC(C=2C=CC=CC=2)=C1 RNOKFJMXGUXDFP-UHFFFAOYSA-N 0.000 description 1
- YRJBZMWQBRBJET-UHFFFAOYSA-N 2-methylsulfonyl-4-phenyl-1,3-oxazole Chemical compound O1C(S(=O)(=O)C)=NC(C=2C=CC=CC=2)=C1 YRJBZMWQBRBJET-UHFFFAOYSA-N 0.000 description 1
- HCSXFDJPRCEICS-UHFFFAOYSA-N 2-phenylhexanamide Chemical compound CCCCC(C(N)=O)C1=CC=CC=C1 HCSXFDJPRCEICS-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 class OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
- CLEJZSNZYFJMKD-UHFFFAOYSA-N 3h-1,3-oxazole-2-thione Chemical class SC1=NC=CO1 CLEJZSNZYFJMKD-UHFFFAOYSA-N 0.000 description 1
- BIMZARKKKXQPQX-UHFFFAOYSA-N 4,5-dimethyl-2-methylsulfinyl-1,3-oxazole Chemical compound CC=1N=C(S(C)=O)OC=1C BIMZARKKKXQPQX-UHFFFAOYSA-N 0.000 description 1
- XEJIHKUDPINBCS-UHFFFAOYSA-N 4,5-dimethyl-3h-1,3-oxazole-2-thione Chemical compound CC=1N=C(S)OC=1C XEJIHKUDPINBCS-UHFFFAOYSA-N 0.000 description 1
- LICCONCDVUJUFN-UHFFFAOYSA-N 4,5-diphenyl-2-phenylsulfanyl-1,3-oxazole Chemical compound C=1C=CC=CC=1SC(O1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 LICCONCDVUJUFN-UHFFFAOYSA-N 0.000 description 1
- DQWSTIDSZQGOTD-UHFFFAOYSA-N 4-[(4-methyl-1,3-oxazol-2-yl)-octanoylamino]butanoic acid Chemical compound CCCCCCCC(=O)N(CCCC(O)=O)C1=NC(C)=CO1 DQWSTIDSZQGOTD-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
- FOQMGINCUIJKBR-UHFFFAOYSA-N 5-ethyl-2-methylsulfanyl-1,3-oxazole Chemical compound CCC1=CN=C(SC)O1 FOQMGINCUIJKBR-UHFFFAOYSA-N 0.000 description 1
- OVMCJOBUFYXXDD-UHFFFAOYSA-N 5-ethyl-2-methylsulfinyl-1,3-oxazole Chemical compound CCC1=CN=C(S(C)=O)O1 OVMCJOBUFYXXDD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OKGRCDVKEPEXFQ-UHFFFAOYSA-N 5-phenyl-3h-1,3-oxazole-2-thione Chemical compound O1C(S)=NC=C1C1=CC=CC=C1 OKGRCDVKEPEXFQ-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 208000001718 Immediate Hypersensitivity Diseases 0.000 description 1
- QCDOTFIMCNNIMQ-UHFFFAOYSA-N N-(2-methoxyethyl)-N-(4-methyl-1,3-oxazol-2-yl)cyclopentanecarboxamide Chemical compound N=1C(C)=COC=1N(CCOC)C(=O)C1CCCC1 QCDOTFIMCNNIMQ-UHFFFAOYSA-N 0.000 description 1
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- 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
- BYRKBBSKUPRTIX-UHFFFAOYSA-N n-butyl-n-(5-cyclohexyl-1,3-oxazol-2-yl)-2-methylpropanamide Chemical compound O1C(N(C(=O)C(C)C)CCCC)=NC=C1C1CCCCC1 BYRKBBSKUPRTIX-UHFFFAOYSA-N 0.000 description 1
- LYZQNEJEVBPKLU-UHFFFAOYSA-N n-butyl-n-(5-ethyl-1,3-oxazol-2-yl)-2-methylpropanamide Chemical compound CCCCN(C(=O)C(C)C)C1=NC=C(CC)O1 LYZQNEJEVBPKLU-UHFFFAOYSA-N 0.000 description 1
- KLYARDOEOYNXNI-UHFFFAOYSA-N n-butyl-n-[4-(4-chlorophenyl)-1,3-oxazol-2-yl]-2-methylpropanamide Chemical compound O1C(N(C(=O)C(C)C)CCCC)=NC(C=2C=CC(Cl)=CC=2)=C1 KLYARDOEOYNXNI-UHFFFAOYSA-N 0.000 description 1
- CUFQQUJWRIUZFF-UHFFFAOYSA-N n-cyclohexyl-n-(4-methyl-1,3-oxazol-2-yl)butanamide Chemical compound N=1C(C)=COC=1N(C(=O)CCC)C1CCCCC1 CUFQQUJWRIUZFF-UHFFFAOYSA-N 0.000 description 1
- JCHYFFPHDIJKJX-UHFFFAOYSA-N n-cyclohexyl-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound N=1C(C)=COC=1N(C(=O)CC)C1CCCCC1 JCHYFFPHDIJKJX-UHFFFAOYSA-N 0.000 description 1
- CVUYHUHTOHGTME-UHFFFAOYSA-N n-cyclopentyl-2-methyl-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound N=1C(C)=COC=1N(C(=O)C(C)C)C1CCCC1 CVUYHUHTOHGTME-UHFFFAOYSA-N 0.000 description 1
- IYQUXKBPGFQMMX-UHFFFAOYSA-N n-cyclopentyl-n-(4-methyl-1,3-oxazol-2-yl)pentanamide Chemical compound N=1C(C)=COC=1N(C(=O)CCCC)C1CCCC1 IYQUXKBPGFQMMX-UHFFFAOYSA-N 0.000 description 1
- QUHWUFXRYOHUJC-UHFFFAOYSA-N n-ethyl-n-(4-methyl-1,3-oxazol-2-yl)butanamide Chemical compound CCCC(=O)N(CC)C1=NC(C)=CO1 QUHWUFXRYOHUJC-UHFFFAOYSA-N 0.000 description 1
- ANMQRLDTUMSFNB-UHFFFAOYSA-N n-ethyl-n-(4-methyl-1,3-oxazol-2-yl)hexanamide Chemical compound CCCCCC(=O)N(CC)C1=NC(C)=CO1 ANMQRLDTUMSFNB-UHFFFAOYSA-N 0.000 description 1
- GJBHVIXTTFEYRY-UHFFFAOYSA-N n-hexyl-2-methyl-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound CCCCCCN(C(=O)C(C)C)C1=NC(C)=CO1 GJBHVIXTTFEYRY-UHFFFAOYSA-N 0.000 description 1
- PTUHRKSMPCEBBS-UHFFFAOYSA-N n-hexyl-n-(4-methyl-1,3-oxazol-2-yl)acetamide Chemical compound CCCCCCN(C(C)=O)C1=NC(C)=CO1 PTUHRKSMPCEBBS-UHFFFAOYSA-N 0.000 description 1
- JQQVBEVWIWFPPZ-UHFFFAOYSA-N n-hexyl-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound CCCCCCN(C(=O)CC)C1=NC(C)=CO1 JQQVBEVWIWFPPZ-UHFFFAOYSA-N 0.000 description 1
- ZMUWBBZXNKHXTD-UHFFFAOYSA-N n-methyl-n-(4-methyl-1,3-oxazol-2-yl)acetamide Chemical compound CC(=O)N(C)C1=NC(C)=CO1 ZMUWBBZXNKHXTD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- PZHNNJXWQYFUTD-UHFFFAOYSA-N phosphorus triiodide Chemical compound IP(I)I PZHNNJXWQYFUTD-UHFFFAOYSA-N 0.000 description 1
- 230000008659 phytopathology Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003169 respiratory stimulant agent Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000012431 wafers Nutrition 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 |
|---|---|
| DE2625229A1 true DE2625229A1 (de) | 1976-12-23 |
Family
ID=10213418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762625229 Withdrawn DE2625229A1 (de) | 1975-06-07 | 1976-06-04 | Verfahren zur herstellung von oxazolderivaten und oxazolderivate |
Country Status (30)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (2)
| 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 |
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 GR GR50869A patent/GR60337B/el unknown
- 1976-06-01 NZ NZ181026A patent/NZ181026A/xx unknown
- 1976-06-01 CA CA253,867A patent/CA1080707A/en not_active Expired
- 1976-06-02 AR AR263482A patent/AR219281A1/es active
- 1976-06-02 SE SE7606227A patent/SE7606227L/xx not_active Application Discontinuation
- 1976-06-02 IE IE1181/76A patent/IE43314B1/en unknown
- 1976-06-02 DK DK243376A patent/DK243376A/da not_active Application Discontinuation
- 1976-06-03 IL IL49710A patent/IL49710A/xx unknown
- 1976-06-03 PT PT65183A patent/PT65183B/pt unknown
- 1976-06-03 HU HU76LI295A patent/HU174777B/hu unknown
- 1976-06-03 YU YU01369/76A patent/YU136976A/xx 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
- 1976-06-04 FR FR7616975A patent/FR2313372A1/fr active Granted
- 1976-06-04 CH CH710576A patent/CH598236A5/xx not_active IP Right Cessation
- 1976-06-04 DD DD193193A patent/DD125347A6/xx unknown
- 1976-06-04 ES ES448591A patent/ES448591A1/es not_active Expired
- 1976-06-04 AT AT412576A patent/AT345278B/de not_active IP Right Cessation
- 1976-06-04 DE DE19762625229 patent/DE2625229A1/de not_active Withdrawn
- 1976-06-04 PH PH18534A patent/PH14307A/en unknown
- 1976-06-04 PL PL1976190128A patent/PL100004B1/pl unknown
- 1976-06-04 JP JP51066028A patent/JPS51146462A/ja active Pending
- 1976-06-04 ZA ZA763336A patent/ZA763336B/xx unknown
- 1976-06-05 RO RO7686351A patent/RO69114A/ro unknown
- 1976-06-07 BG BG033393A patent/BG25516A3/xx unknown
- 1976-06-07 SU SU762367752A patent/SU610490A3/ru active
- 1976-06-07 CS CS763747A patent/CS190536B2/cs unknown
- 1976-06-07 MX MX000274U patent/MX3140E/es unknown
- 1976-06-08 NL NL7606177A patent/NL7606177A/xx not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8162 | Independent application | ||
| 8110 | Request for examination paragraph 44 | ||
| 8181 | Inventor (new situation) |
Free format text: HARRISON, ROGER GARRICK, FARNBOROUGH, HAMPSHIRE, GB |
|
| 8139 | Disposal/non-payment of the annual fee |