JPH0374224B2 - - Google Patents
Info
- Publication number
- JPH0374224B2 JPH0374224B2 JP22334083A JP22334083A JPH0374224B2 JP H0374224 B2 JPH0374224 B2 JP H0374224B2 JP 22334083 A JP22334083 A JP 22334083A JP 22334083 A JP22334083 A JP 22334083A JP H0374224 B2 JPH0374224 B2 JP H0374224B2
- Authority
- JP
- Japan
- Prior art keywords
- propanethiol
- group
- nitromethylene
- tetrahydro
- yield
- 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
- -1 nitromethylene group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002474 experimental method Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- FYTHQYLRQAISTJ-UHFFFAOYSA-N 3-(methylamino)propane-1-thiol Chemical compound CNCCCS FYTHQYLRQAISTJ-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 239000002585 base Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- CTFMCQGUXONREY-UHFFFAOYSA-N 1,1-dichloro-2-nitroethene Chemical group [O-][N+](=O)C=C(Cl)Cl CTFMCQGUXONREY-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- BKOLIJBSENFKNE-UHFFFAOYSA-N 1,1,2-trichloro-2-nitroethene Chemical group [O-][N+](=O)C(Cl)=C(Cl)Cl BKOLIJBSENFKNE-UHFFFAOYSA-N 0.000 description 3
- ONTZYYWACSMBPU-UHFFFAOYSA-N 1-(nitromethylidene)-2H-1,3-thiazine Chemical compound [N+](=O)([O-])C=S1CN=CC=C1 ONTZYYWACSMBPU-UHFFFAOYSA-N 0.000 description 3
- NZSNWIOVGALACV-UHFFFAOYSA-N 2-(methylamino)ethanethiol Chemical group CNCCS NZSNWIOVGALACV-UHFFFAOYSA-N 0.000 description 3
- QIMMEUAHMKCLOI-UHFFFAOYSA-N 3-(prop-2-ynylamino)propane-1-thiol Chemical compound SCCCNCC#C QIMMEUAHMKCLOI-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QEPNJQRZLOIYFS-UHFFFAOYSA-N 1,1-dibromo-2-nitroethene Chemical group [O-][N+](=O)C=C(Br)Br QEPNJQRZLOIYFS-UHFFFAOYSA-N 0.000 description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 2
- PMEGPZUSWYUAQN-UHFFFAOYSA-N 3-(benzylamino)propane-1-thiol Chemical compound SCCCNCC1=CC=CC=C1 PMEGPZUSWYUAQN-UHFFFAOYSA-N 0.000 description 2
- RDYRRCJNRVLTLR-UHFFFAOYSA-N 3-(cyclohexylamino)propane-1-thiol Chemical compound SCCCNC1CCCCC1 RDYRRCJNRVLTLR-UHFFFAOYSA-N 0.000 description 2
- XXWMNLPFZNNFHM-UHFFFAOYSA-N 3-(hexylamino)propane-1-thiol Chemical compound CCCCCCNCCCS XXWMNLPFZNNFHM-UHFFFAOYSA-N 0.000 description 2
- DPDHDSXYEXSENQ-UHFFFAOYSA-N 3-(propan-2-ylamino)propane-1-thiol Chemical compound CC(C)NCCCS DPDHDSXYEXSENQ-UHFFFAOYSA-N 0.000 description 2
- HDZQSPCEILQRNE-UHFFFAOYSA-N 3-ethyl-2-(nitromethylidene)-1,3-thiazinane Chemical compound CCN1CCCSC1=C[N+]([O-])=O HDZQSPCEILQRNE-UHFFFAOYSA-N 0.000 description 2
- RVNXOEMSROXCBP-UHFFFAOYSA-N 3-methyl-2-(nitromethylidene)-1,3-thiazinane Chemical compound CN1CCCSC1=C[N+]([O-])=O RVNXOEMSROXCBP-UHFFFAOYSA-N 0.000 description 2
- FVSFQZRTCQYECI-UHFFFAOYSA-N 4-(methylamino)butane-1-thiol Chemical compound CNCCCCS FVSFQZRTCQYECI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LMESVXSPWBSGFV-UHFFFAOYSA-N 1,1,2-tribromo-2-nitroethene Chemical group [O-][N+](=O)C(Br)=C(Br)Br LMESVXSPWBSGFV-UHFFFAOYSA-N 0.000 description 1
- JHCXOMYJMDHJOP-UHFFFAOYSA-N 1,1-dichloro-2-nitrobut-1-ene Chemical group CCC(=C(Cl)Cl)[N+]([O-])=O JHCXOMYJMDHJOP-UHFFFAOYSA-N 0.000 description 1
- IQBUGJGIXCDOFT-UHFFFAOYSA-N 1,1-dichloro-2-nitroprop-1-ene Chemical group ClC(Cl)=C(C)[N+]([O-])=O IQBUGJGIXCDOFT-UHFFFAOYSA-N 0.000 description 1
- WTKPMGHABVZBRB-UHFFFAOYSA-N 1,1-difluoro-2-nitroethene Chemical group [O-][N+](=O)C=C(F)F WTKPMGHABVZBRB-UHFFFAOYSA-N 0.000 description 1
- QRKFSSBVDJBSNP-UHFFFAOYSA-N 1,1-diiodo-2-nitroethene Chemical group [O-][N+](=O)C=C(I)I QRKFSSBVDJBSNP-UHFFFAOYSA-N 0.000 description 1
- DDDWOMIVMIHAEN-UHFFFAOYSA-N 1,3-thiazinane-2-thione Chemical compound S=C1NCCCS1 DDDWOMIVMIHAEN-UHFFFAOYSA-N 0.000 description 1
- PKGPCXWPHCSJNL-UHFFFAOYSA-N 1-bromo-1,2-dichloro-2-nitroethene Chemical group [O-][N+](=O)C(Cl)=C(Cl)Br PKGPCXWPHCSJNL-UHFFFAOYSA-N 0.000 description 1
- KBORGWRLSHNLFT-UHFFFAOYSA-N 1-bromo-1-chloro-2-nitroethene Chemical group [O-][N+](=O)C=C(Cl)Br KBORGWRLSHNLFT-UHFFFAOYSA-N 0.000 description 1
- LZBLMMNDKAQNGJ-UHFFFAOYSA-N 1-bromo-1-chloro-2-nitroprop-1-ene Chemical group ClC(Br)=C(C)[N+]([O-])=O LZBLMMNDKAQNGJ-UHFFFAOYSA-N 0.000 description 1
- LSBSTDOEUPUHBE-UHFFFAOYSA-N 1-bromo-1-chlorobut-1-ene Chemical group CCC=C(Cl)Br LSBSTDOEUPUHBE-UHFFFAOYSA-N 0.000 description 1
- XNQLCBFHVABMGE-UHFFFAOYSA-N 1-bromo-1-nitroethene Chemical group [O-][N+](=O)C(Br)=C XNQLCBFHVABMGE-UHFFFAOYSA-N 0.000 description 1
- GKOGHAJFAKXNOW-UHFFFAOYSA-N 1-bromo-2,2-dichloro-1-nitroethene Chemical group [O-][N+](=O)C(Br)=C(Cl)Cl GKOGHAJFAKXNOW-UHFFFAOYSA-N 0.000 description 1
- LDJADHZNGVTQJD-UHFFFAOYSA-N 2-(benzylamino)ethanethiol Chemical compound SCCNCC1=CC=CC=C1 LDJADHZNGVTQJD-UHFFFAOYSA-N 0.000 description 1
- HQMCMJWBJSSFFS-UHFFFAOYSA-N 2-(cyclohexylamino)ethanethiol Chemical compound SCCNC1CCCCC1 HQMCMJWBJSSFFS-UHFFFAOYSA-N 0.000 description 1
- KMTRYVQPHVFAFJ-UHFFFAOYSA-N 2-(ethylamino)ethanethiol Chemical compound CCNCCS KMTRYVQPHVFAFJ-UHFFFAOYSA-N 0.000 description 1
- KMQYLYBONJSUPB-UHFFFAOYSA-N 2-(nitromethylidene)-3-prop-2-ynyl-1,3-thiazinane Chemical compound [O-][N+](=O)C=C1SCCCN1CC#C KMQYLYBONJSUPB-UHFFFAOYSA-N 0.000 description 1
- VGAUDMMWNYUCAU-UHFFFAOYSA-N 2-(prop-2-ynylamino)ethanethiol Chemical compound SCCNCC#C VGAUDMMWNYUCAU-UHFFFAOYSA-N 0.000 description 1
- RVHUIQSWHPZCCP-UHFFFAOYSA-N 2-(propylamino)ethanethiol Chemical compound CCCNCCS RVHUIQSWHPZCCP-UHFFFAOYSA-N 0.000 description 1
- DGGPBPNVUGTTCU-UHFFFAOYSA-N 2-[chloro(nitro)methylidene]-3-cyclohexyl-1,3-thiazinane Chemical compound C1(CCCCC1)N1C(SCCC1)=C(Cl)[N+](=O)[O-] DGGPBPNVUGTTCU-UHFFFAOYSA-N 0.000 description 1
- VTRGSTQDFXNATL-UHFFFAOYSA-N 2-[chloro(nitro)methylidene]-3-ethyl-1,3-thiazinane Chemical compound CCN1CCCSC1=C(Cl)[N+]([O-])=O VTRGSTQDFXNATL-UHFFFAOYSA-N 0.000 description 1
- CIIXFAQDXXRRSL-UHFFFAOYSA-N 2-[chloro(nitro)methylidene]-3-methyl-1,3-thiazinane Chemical compound CN1C(SCCC1)=C(Cl)[N+](=O)[O-] CIIXFAQDXXRRSL-UHFFFAOYSA-N 0.000 description 1
- LNUGHNDVERZEPT-UHFFFAOYSA-N 2-[chloro(nitro)methylidene]-3-methyl-1,3-thiazolidine Chemical compound CN1CCSC1=C(Cl)[N+]([O-])=O LNUGHNDVERZEPT-UHFFFAOYSA-N 0.000 description 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 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 description 1
- GHIRQLDGISSARC-UHFFFAOYSA-N 3-(cyclododecylamino)propane-1-thiol Chemical compound SCCCNC1CCCCCCCCCCC1 GHIRQLDGISSARC-UHFFFAOYSA-N 0.000 description 1
- DYPYVNLPDQLUQR-UHFFFAOYSA-N 3-(cyclooctylamino)propane-1-thiol Chemical compound SCCCNC1CCCCCCC1 DYPYVNLPDQLUQR-UHFFFAOYSA-N 0.000 description 1
- BODXNTFTUVZKNG-UHFFFAOYSA-N 3-(decylamino)propane-1-thiol Chemical compound CCCCCCCCCCNCCCS BODXNTFTUVZKNG-UHFFFAOYSA-N 0.000 description 1
- WSGLOWHDPJYPHI-UHFFFAOYSA-N 3-(dodecylamino)propane-1-thiol Chemical compound CCCCCCCCCCCCNCCCS WSGLOWHDPJYPHI-UHFFFAOYSA-N 0.000 description 1
- YLBIOIADVQMNJP-UHFFFAOYSA-N 3-(propylamino)propane-1-thiol Chemical compound CCCNCCCS YLBIOIADVQMNJP-UHFFFAOYSA-N 0.000 description 1
- LTFPFYONKDCLSQ-UHFFFAOYSA-N 3-benzyl-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)C=C1SCCCN1CC1=CC=CC=C1 LTFPFYONKDCLSQ-UHFFFAOYSA-N 0.000 description 1
- DMJWWTCMZGZWKB-UHFFFAOYSA-N 3-benzyl-2-[chloro(nitro)methylidene]-1,3-thiazinane Chemical compound C(C1=CC=CC=C1)N1C(SCCC1)=C(Cl)[N+](=O)[O-] DMJWWTCMZGZWKB-UHFFFAOYSA-N 0.000 description 1
- OOOYOJCOCOARGC-UHFFFAOYSA-N 3-cyclohexyl-2-(nitromethylidene)-1,3-thiazepane Chemical compound [O-][N+](=O)C=C1SCCCCN1C1CCCCC1 OOOYOJCOCOARGC-UHFFFAOYSA-N 0.000 description 1
- PPIVIKVOLMOYJT-UHFFFAOYSA-N 3-cyclohexyl-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)C=C1SCCCN1C1CCCCC1 PPIVIKVOLMOYJT-UHFFFAOYSA-N 0.000 description 1
- ALZSECYEBWDHSS-UHFFFAOYSA-N 3-methyl-2-(nitromethylidene)-1,3-thiazepane Chemical compound CN1CCCCSC1=C[N+]([O-])=O ALZSECYEBWDHSS-UHFFFAOYSA-N 0.000 description 1
- SNQRNCJUWHEPBW-UHFFFAOYSA-N 3-methyl-2-(nitromethylidene)-1,3-thiazolidine Chemical compound CN1CCSC1=C[N+]([O-])=O SNQRNCJUWHEPBW-UHFFFAOYSA-N 0.000 description 1
- YHEZUKAFXVHLFI-UHFFFAOYSA-N 4-(benzylamino)butane-1-thiol Chemical compound SCCCCNCC1=CC=CC=C1 YHEZUKAFXVHLFI-UHFFFAOYSA-N 0.000 description 1
- KZSNCBSYFUHVNZ-UHFFFAOYSA-N 4-(cyclohexylamino)butane-1-thiol Chemical compound SCCCCNC1CCCCC1 KZSNCBSYFUHVNZ-UHFFFAOYSA-N 0.000 description 1
- ROQFEQWXZDPPND-UHFFFAOYSA-N 4-(ethylamino)butane-1-thiol Chemical compound CCNCCCCS ROQFEQWXZDPPND-UHFFFAOYSA-N 0.000 description 1
- WLYSDYUFTQPJGQ-UHFFFAOYSA-N 4-(propylamino)butane-1-thiol Chemical compound CCCNCCCCS WLYSDYUFTQPJGQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000004912 thiazepines Chemical class 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22334083A JPS60116676A (ja) | 1983-11-29 | 1983-11-29 | 側鎖にニトロメチレン基を有するヘテロ環化合物の製法 |
| US06/569,983 US4665172A (en) | 1983-01-28 | 1984-01-11 | Process for producing heterocyclic compound having nitromethylene group as the side chain group |
| CA000445262A CA1208213A (en) | 1983-01-28 | 1984-01-13 | Process for producing heterocyclic compound having nitromethylene group as the side chain group |
| KR1019840000246A KR860001183B1 (ko) | 1983-01-28 | 1984-01-20 | 측쇄기로서 니트로메틸렌기를 갖는 헤테로고리 화합물의 제조방법 |
| EP84100712A EP0115323B1 (de) | 1983-01-28 | 1984-01-24 | Verfahren zur Herstellung von einer durch Nitromethylenrest substituierten heterocyclischen Verbindung |
| DE8484100712T DE3483049D1 (de) | 1983-01-28 | 1984-01-24 | Verfahren zur herstellung von einer durch nitromethylenrest substituierten heterocyclischen verbindung. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22334083A JPS60116676A (ja) | 1983-11-29 | 1983-11-29 | 側鎖にニトロメチレン基を有するヘテロ環化合物の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60116676A JPS60116676A (ja) | 1985-06-24 |
| JPH0374224B2 true JPH0374224B2 (de) | 1991-11-26 |
Family
ID=16796622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22334083A Granted JPS60116676A (ja) | 1983-01-28 | 1983-11-29 | 側鎖にニトロメチレン基を有するヘテロ環化合物の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60116676A (de) |
-
1983
- 1983-11-29 JP JP22334083A patent/JPS60116676A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60116676A (ja) | 1985-06-24 |
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