JPH0124143B2 - - Google Patents
Info
- Publication number
- JPH0124143B2 JPH0124143B2 JP17792981A JP17792981A JPH0124143B2 JP H0124143 B2 JPH0124143 B2 JP H0124143B2 JP 17792981 A JP17792981 A JP 17792981A JP 17792981 A JP17792981 A JP 17792981A JP H0124143 B2 JPH0124143 B2 JP H0124143B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- alkyl group
- phenyl
- alkyl
- 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.)
- Expired
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims description 12
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- ZBVZOMFYISPWMD-UHFFFAOYSA-N amino thiohypochlorite Chemical class NSCl ZBVZOMFYISPWMD-UHFFFAOYSA-N 0.000 claims description 7
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims description 7
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000002019 disulfides Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 37
- 150000001875 compounds Chemical class 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000001308 synthesis method Methods 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- -1 2,3-dihydro-2,2-dimethylbenzofuran-7-yl Chemical group 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000007514 bases Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229910001868 water Inorganic materials 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- YZPXDEXTKPFTGC-UHFFFAOYSA-N ethyl 2-(butylamino)propanoate Chemical compound CCCCNC(C)C(=O)OCC YZPXDEXTKPFTGC-UHFFFAOYSA-N 0.000 description 2
- AMBDTBHJFINMSE-UHFFFAOYSA-N ethyl 2-acetamidoacetate Chemical compound CCOC(=O)CNC(C)=O AMBDTBHJFINMSE-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons 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
- 239000002917 insecticide Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- VXGABWCSZZWXPC-UHFFFAOYSA-N methyl 2-(methylamino)acetate Chemical compound CNCC(=O)OC VXGABWCSZZWXPC-UHFFFAOYSA-N 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RDJUHLUBPADHNP-UHFFFAOYSA-N 1,2,3,5-tetrahydroxybenzene Chemical compound OC1=CC(O)=C(O)C(O)=C1 RDJUHLUBPADHNP-UHFFFAOYSA-N 0.000 description 1
- OJUIRUMDLUMSTN-UHFFFAOYSA-N 2-(benzylamino)acetonitrile;hydrochloride Chemical compound Cl.N#CCNCC1=CC=CC=C1 OJUIRUMDLUMSTN-UHFFFAOYSA-N 0.000 description 1
- SPMMZKAWNAKPJM-UHFFFAOYSA-N 2-(butylamino)acetonitrile Chemical compound CCCCNCC#N SPMMZKAWNAKPJM-UHFFFAOYSA-N 0.000 description 1
- VXAOLDZFARINGE-UHFFFAOYSA-N 2-(ethylamino)acetonitrile Chemical compound CCNCC#N VXAOLDZFARINGE-UHFFFAOYSA-N 0.000 description 1
- PVVRRUUMHFWFQV-UHFFFAOYSA-N 2-(methylamino)acetonitrile Chemical compound CNCC#N PVVRRUUMHFWFQV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- HVNPFQOMBNYVMB-UHFFFAOYSA-N butyl 2-(methylamino)acetate Chemical compound CCCCOC(=O)CNC HVNPFQOMBNYVMB-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- SBPUJTNHAUBDKF-UHFFFAOYSA-N ethyl 2-(2-cyanoethylamino)acetate Chemical compound CCOC(=O)CNCCC#N SBPUJTNHAUBDKF-UHFFFAOYSA-N 0.000 description 1
- XJBLZCHTARFLLD-UHFFFAOYSA-N ethyl 2-(2-methylpropylamino)acetate Chemical compound CCOC(=O)CNCC(C)C XJBLZCHTARFLLD-UHFFFAOYSA-N 0.000 description 1
- JZCIUMVCWIEEQX-UHFFFAOYSA-N ethyl 2-(3-methylanilino)acetate Chemical compound CCOC(=O)CNC1=CC=CC(C)=C1 JZCIUMVCWIEEQX-UHFFFAOYSA-N 0.000 description 1
- XDAVIDCHNYCQCT-UHFFFAOYSA-N ethyl 2-(3-methylbutylamino)propanoate Chemical compound CCOC(=O)C(C)NCCC(C)C XDAVIDCHNYCQCT-UHFFFAOYSA-N 0.000 description 1
- TZJRPKDPYLAMJZ-UHFFFAOYSA-N ethyl 2-(4-methoxyanilino)acetate Chemical compound CCOC(=O)CNC1=CC=C(OC)C=C1 TZJRPKDPYLAMJZ-UHFFFAOYSA-N 0.000 description 1
- KTRUZIMBKAONKB-UHFFFAOYSA-N ethyl 2-(butan-2-ylamino)acetate Chemical compound CCOC(=O)CNC(C)CC KTRUZIMBKAONKB-UHFFFAOYSA-N 0.000 description 1
- OJFGRDHUZSJJPB-UHFFFAOYSA-N ethyl 2-(butylamino)acetate Chemical compound CCCCNCC(=O)OCC OJFGRDHUZSJJPB-UHFFFAOYSA-N 0.000 description 1
- HJHAOMCORINKOB-UHFFFAOYSA-N ethyl 2-(cyanomethylamino)acetate Chemical compound CCOC(=O)CNCC#N HJHAOMCORINKOB-UHFFFAOYSA-N 0.000 description 1
- DITDYMTYUDGGGF-UHFFFAOYSA-N ethyl 2-(cyanomethylamino)propanoate Chemical compound CCOC(=O)C(C)NCC#N DITDYMTYUDGGGF-UHFFFAOYSA-N 0.000 description 1
- NHRFJPKXIYYFMX-UHFFFAOYSA-N ethyl 2-(cyclohexylamino)acetate Chemical compound CCOC(=O)CNC1CCCCC1 NHRFJPKXIYYFMX-UHFFFAOYSA-N 0.000 description 1
- NRMPJIHWGVBZBB-UHFFFAOYSA-N ethyl 2-(ethylamino)acetate Chemical compound CCNCC(=O)OCC NRMPJIHWGVBZBB-UHFFFAOYSA-N 0.000 description 1
- LCMDFUNTIZKNJK-UHFFFAOYSA-N ethyl 2-(hexylamino)propanoate Chemical compound CCCCCCNC(C)C(=O)OCC LCMDFUNTIZKNJK-UHFFFAOYSA-N 0.000 description 1
- LNYUJLIYAHJNNO-UHFFFAOYSA-N ethyl 2-(methoxycarbonylamino)acetate Chemical compound CCOC(=O)CNC(=O)OC LNYUJLIYAHJNNO-UHFFFAOYSA-N 0.000 description 1
- BTKSUULMJNNXHG-UHFFFAOYSA-N ethyl 2-(methylamino)acetate Chemical compound CCOC(=O)CNC BTKSUULMJNNXHG-UHFFFAOYSA-N 0.000 description 1
- KHRLPZJTPHCMSQ-UHFFFAOYSA-N ethyl 2-(methylamino)propanoate Chemical compound CCOC(=O)C(C)NC KHRLPZJTPHCMSQ-UHFFFAOYSA-N 0.000 description 1
- PYZXUPBTKMMQGZ-UHFFFAOYSA-N ethyl 2-(octylamino)acetate Chemical compound CCCCCCCCNCC(=O)OCC PYZXUPBTKMMQGZ-UHFFFAOYSA-N 0.000 description 1
- CWPWNWCAOJRJJT-UHFFFAOYSA-N ethyl 2-(phenoxycarbonylamino)acetate Chemical compound CCOC(=O)CNC(=O)OC1=CC=CC=C1 CWPWNWCAOJRJJT-UHFFFAOYSA-N 0.000 description 1
- ROGQHXXFNVNMSC-UHFFFAOYSA-N ethyl 2-(propan-2-ylamino)acetate Chemical compound CCOC(=O)CNC(C)C ROGQHXXFNVNMSC-UHFFFAOYSA-N 0.000 description 1
- JBIONIMUHCHUOW-UHFFFAOYSA-N ethyl 2-(propan-2-ylamino)propanoate Chemical compound CCOC(=O)C(C)NC(C)C JBIONIMUHCHUOW-UHFFFAOYSA-N 0.000 description 1
- XKFRTCBBCLBPOA-UHFFFAOYSA-N ethyl 2-(propanoylamino)acetate Chemical compound CCOC(=O)CNC(=O)CC XKFRTCBBCLBPOA-UHFFFAOYSA-N 0.000 description 1
- JJUSZJBGNONFQT-UHFFFAOYSA-N ethyl 2-(propylamino)acetate Chemical compound CCCNCC(=O)OCC JJUSZJBGNONFQT-UHFFFAOYSA-N 0.000 description 1
- KQSPDAGLBCHMTH-UHFFFAOYSA-N ethyl 2-(tert-butylamino)propanoate Chemical compound CCOC(=O)C(C)NC(C)(C)C KQSPDAGLBCHMTH-UHFFFAOYSA-N 0.000 description 1
- GSHWWBSVIZYONT-UHFFFAOYSA-N ethyl 2-[(2-chloroacetyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)CCl GSHWWBSVIZYONT-UHFFFAOYSA-N 0.000 description 1
- LMJVHEMAGFYVBY-UHFFFAOYSA-N ethyl 2-[(2-ethoxy-2-oxoethyl)amino]butanoate Chemical compound CCOC(=O)CNC(CC)C(=O)OCC LMJVHEMAGFYVBY-UHFFFAOYSA-N 0.000 description 1
- IIBDNCRATXAUMF-UHFFFAOYSA-N ethyl 2-[(2-ethoxy-2-oxoethyl)amino]propanoate Chemical compound CCOC(=O)CNC(C)C(=O)OCC IIBDNCRATXAUMF-UHFFFAOYSA-N 0.000 description 1
- XYVZUPHHGNHQHN-UHFFFAOYSA-N ethyl 2-[(4-chlorobenzoyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=C(Cl)C=C1 XYVZUPHHGNHQHN-UHFFFAOYSA-N 0.000 description 1
- LDTGTJKHPGIRGV-UHFFFAOYSA-N ethyl 2-[(4-chlorophenyl)methylamino]acetate Chemical compound CCOC(=O)CNCC1=CC=C(Cl)C=C1 LDTGTJKHPGIRGV-UHFFFAOYSA-N 0.000 description 1
- QZLMPLDNZZQWOX-UHFFFAOYSA-N ethyl 2-[(4-methylphenyl)methylamino]acetate Chemical compound CCOC(=O)CNCC1=CC=C(C)C=C1 QZLMPLDNZZQWOX-UHFFFAOYSA-N 0.000 description 1
- WZLAJHNLDCWPGH-UHFFFAOYSA-N ethyl 2-[(4-methylphenyl)sulfonylamino]acetate Chemical compound CCOC(=O)CNS(=O)(=O)C1=CC=C(C)C=C1 WZLAJHNLDCWPGH-UHFFFAOYSA-N 0.000 description 1
- CXDAFOJQFCKBLP-UHFFFAOYSA-N ethyl 2-[acetyl(chlorosulfanyl)amino]acetate Chemical compound CCOC(=O)CN(SCl)C(C)=O CXDAFOJQFCKBLP-UHFFFAOYSA-N 0.000 description 1
- MXHSXMBHUOBBPL-UHFFFAOYSA-N ethyl 2-[chlorosulfanyl(methoxycarbonyl)amino]acetate Chemical compound CCOC(=O)CN(SCl)C(=O)OC MXHSXMBHUOBBPL-UHFFFAOYSA-N 0.000 description 1
- MLSGRWDEDYJNER-UHFFFAOYSA-N ethyl 2-anilinoacetate Chemical compound CCOC(=O)CNC1=CC=CC=C1 MLSGRWDEDYJNER-UHFFFAOYSA-N 0.000 description 1
- PTXRQIPIELXJFH-UHFFFAOYSA-N ethyl 2-benzamidoacetate Chemical compound CCOC(=O)CNC(=O)C1=CC=CC=C1 PTXRQIPIELXJFH-UHFFFAOYSA-N 0.000 description 1
- FTKLDWGDFWLILC-UHFFFAOYSA-N ethyl 3-[butyl(chlorosulfanyl)amino]propanoate Chemical compound CCCCN(SCl)CCC(=O)OCC FTKLDWGDFWLILC-UHFFFAOYSA-N 0.000 description 1
- QQFIULJNMVXXQZ-UHFFFAOYSA-N ethyl 3-[chlorosulfanyl(propan-2-yl)amino]propanoate Chemical compound CCOC(=O)CCN(SCl)C(C)C QQFIULJNMVXXQZ-UHFFFAOYSA-N 0.000 description 1
- ATJAIVKHTGMHPH-UHFFFAOYSA-N ethyl 4-[(2-ethoxy-2-oxoethyl)amino]butanoate Chemical compound CCOC(=O)CCCNCC(=O)OCC ATJAIVKHTGMHPH-UHFFFAOYSA-N 0.000 description 1
- LXRRVDLNCROODH-UHFFFAOYSA-N ethyl n-(2-cyanoethyl)carbamate Chemical compound CCOC(=O)NCCC#N LXRRVDLNCROODH-UHFFFAOYSA-N 0.000 description 1
- AHGQESFVDCNOGJ-UHFFFAOYSA-N ethyl n-(cyanomethyl)carbamate Chemical compound CCOC(=O)NCC#N AHGQESFVDCNOGJ-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NELVBJNELOBGSL-UHFFFAOYSA-N methyl 2-(butylamino)propanoate Chemical compound CCCCNC(C)C(=O)OC NELVBJNELOBGSL-UHFFFAOYSA-N 0.000 description 1
- DRMGMMWXWKLKAI-UHFFFAOYSA-N methyl n-(cyanomethyl)carbamate Chemical compound COC(=O)NCC#N DRMGMMWXWKLKAI-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17792981A JPS5877860A (ja) | 1981-11-05 | 1981-11-05 | アミノスルフエニルクロリド誘導体及びその製造法 |
| CA000399286A CA1188706A (en) | 1981-03-30 | 1982-03-24 | Aminosulfenyl chloride derivatives, process for preparing the same |
| DE3211087A DE3211087C2 (de) | 1981-03-30 | 1982-03-25 | Aminosulfenylchloridderivate, Verfahren zu deren Herstellung und deren Verwendung |
| US06/361,931 US4421693A (en) | 1981-03-30 | 1982-03-25 | Aminosulfenyl chloride derivatives |
| AR288882A AR230833A1 (es) | 1981-03-30 | 1982-03-26 | Derivados de aminosulfeniloloruro,procedimiento para su preparacion y procedimiento para la preparacion de derivados de carbamato utiles como compuestos insecticidas,acaricidas y nematocidas a partir de dichos derivados |
| ES510885A ES510885A0 (es) | 1981-03-30 | 1982-03-27 | Procedimiento de preparar derivados de cloruro de aminosulfenilo, utiles para insecticidas |
| GR67741A GR75920B (enrdf_load_stackoverflow) | 1981-03-30 | 1982-03-29 | |
| IT48109/82A IT1147830B (it) | 1981-03-30 | 1982-03-29 | Derivati di amminosolfenilcloruri,procedimento per prepararli nonche' per preparare da essi derivati carbammati utili come pesticidi |
| MX192032A MX160562A (es) | 1981-03-30 | 1982-03-29 | Un proceso para preparar derivados de cloruro de aninosulfenilo |
| NZ200163A NZ200163A (en) | 1981-03-30 | 1982-03-29 | Aminosulphenyl chloride derivatives and methods for their preparation |
| NL8201290A NL8201290A (nl) | 1981-03-30 | 1982-03-29 | Aminosulfenylchloridederivaten, werkwijze voor het bereiden daarvan en werkwijze voor het bereiden van carbamaatderivaten, die geschikt zijn als insekticiden, miticiden of nematociden. |
| SE8202001A SE456578B (sv) | 1981-03-30 | 1982-03-29 | Aminosulfenylkloridderivat, forfarande for framstellning derav samt forfarande for framstellning av karbamatderivat, som er anvendbara sasom insekticida, miticida eller nematocida foreningar |
| CS822222A CS237330B2 (en) | 1981-11-05 | 1982-03-29 | Processing of aminosulphenylchloride derivatives |
| SU823414098A SU1243621A3 (ru) | 1981-03-30 | 1982-03-29 | Способ получени производных аминосульфенилхлорида |
| CH1915/82A CH653016A5 (fr) | 1981-03-30 | 1982-03-29 | Derives du chlorure d'aminosulfenyle, procede pour la preparation de ceux-ci et utilisation de ces derives pour la preparation de carbamates. |
| EG16782A EG15607A (en) | 1981-05-22 | 1982-03-29 | Aminosulfenyl chloride derivatives,process for preparing the same,and process for preparing carbamate derivatives useful as insecticidal,miticidal or nematocidal compounds |
| GB8209194A GB2096994B (en) | 1981-03-30 | 1982-03-29 | Aminosulfenyl chloride derivatives and process for preparing carbamate derivatives useful as ins |
| NZ20982782A NZ209827A (en) | 1981-03-30 | 1982-03-29 | Process for the preparation of 2,3-dihydro-2,2-dimethylbenzofuran-7-yl n-(n,n-disubstituted aminosulphenyl)-n-methyl carbamate derivatives |
| FR8205475A FR2502616B1 (fr) | 1981-03-30 | 1982-03-30 | Chlorures d'aminosulfenyle, procede pour leur preparation et leur utilisation dans la preparation de carbamates possedant des proprietes insecticides, miticides ou nematocides |
| IL65384A IL65384A (en) | 1981-03-30 | 1982-03-30 | Aminosulfenyl chloride derivatives,their preparation and their use as intermediates for preparing carbamate derivatives |
| KR8201384A KR880002299B1 (ko) | 1981-03-30 | 1982-03-30 | 아미노설페닐 클로라이드 유도체 및 카바메이트 유도체의 제조방법 |
| IN354/CAL/82A IN156106B (enrdf_load_stackoverflow) | 1981-03-30 | 1982-03-30 | |
| TR21303A TR21303A (tr) | 1981-03-30 | 1982-03-30 | Aminosulfenil klor*r t*revleri,bunlari hazirlamaya mahsus usul ve ensektisid,mitisid veya nematosid bilesikler olarak kullanilmaya elverisli olan karbomat t*revlerini hazirlamaya mahsus usul |
| DD82238568A DD204251A5 (de) | 1981-03-30 | 1982-03-30 | Verfahren zur herstellung von aminosulfenylchloridderivaten |
| MA19629A MA19424A1 (fr) | 1981-03-30 | 1982-03-30 | Chlorures de sulfenyle, procede pour leur preparation et celle de carbamates servant de composes insecticides acaricides ou nematicides |
| HU97282A HU193263B (en) | 1981-03-30 | 1982-03-30 | Process for preparing amino-sulphenyl-chloride derivatives |
| AU82143/82A AU545481B2 (en) | 1981-03-30 | 1982-03-30 | Aminosulfenyl chlorides and preparation of 7-benzofuryl- n-(aminosulfenyl)carbamates |
| DD82246179A DD208803A5 (de) | 1981-03-30 | 1982-03-30 | Verfahren zur herstellung eines 2,3-dihydro-2,2-dimethylbenzofuran-7-yl-n-(n,n-disubstituierten aminosulfenyl)-n-methyl-carbamats |
| ES521601A ES521601A0 (es) | 1981-03-30 | 1983-03-31 | Metodo de obtencion de derivados n-metilcarbamaticos utiles para insecticidas. |
| CA000453645A CA1187089A (en) | 1981-03-30 | 1984-05-04 | Process for preparing carbamate derivatives useful as insecticidal, miticidal or nematocidal compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17792981A JPS5877860A (ja) | 1981-11-05 | 1981-11-05 | アミノスルフエニルクロリド誘導体及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5877860A JPS5877860A (ja) | 1983-05-11 |
| JPH0124143B2 true JPH0124143B2 (enrdf_load_stackoverflow) | 1989-05-10 |
Family
ID=16039531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17792981A Granted JPS5877860A (ja) | 1981-03-30 | 1981-11-05 | アミノスルフエニルクロリド誘導体及びその製造法 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5877860A (enrdf_load_stackoverflow) |
| CS (1) | CS237330B2 (enrdf_load_stackoverflow) |
-
1981
- 1981-11-05 JP JP17792981A patent/JPS5877860A/ja active Granted
-
1982
- 1982-03-29 CS CS822222A patent/CS237330B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5877860A (ja) | 1983-05-11 |
| CS222282A2 (en) | 1984-12-14 |
| CS237330B2 (en) | 1985-07-16 |
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