JPH0373546B2 - - Google Patents
Info
- Publication number
- JPH0373546B2 JPH0373546B2 JP1135683A JP1135683A JPH0373546B2 JP H0373546 B2 JPH0373546 B2 JP H0373546B2 JP 1135683 A JP1135683 A JP 1135683A JP 1135683 A JP1135683 A JP 1135683A JP H0373546 B2 JPH0373546 B2 JP H0373546B2
- Authority
- JP
- Japan
- Prior art keywords
- nitromethylene
- solution
- compound
- 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
- 150000001875 compounds Chemical class 0.000 claims description 20
- -1 nitromethylene group Chemical group 0.000 claims description 18
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000243 solution Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- LZTIMERBDGGAJD-UHFFFAOYSA-N nithiazine Chemical compound [O-][N+](=O)C=C1NCCCS1 LZTIMERBDGGAJD-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- CTFMCQGUXONREY-UHFFFAOYSA-N 1,1-dichloro-2-nitroethene Chemical group [O-][N+](=O)C=C(Cl)Cl CTFMCQGUXONREY-UHFFFAOYSA-N 0.000 description 6
- IYGAMTQMILRCCI-UHFFFAOYSA-N 3-aminopropane-1-thiol Chemical compound NCCCS IYGAMTQMILRCCI-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
- 239000002994 raw material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-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
- RIRRYXTXJAZPMP-UHFFFAOYSA-N 4-aminobutane-1-thiol Chemical compound NCCCCS RIRRYXTXJAZPMP-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
- IDEZECZCLMOIJN-UHFFFAOYSA-N 2-(nitromethylidene)-1,3-thiazolidine Chemical compound [O-][N+](=O)C=C1NCCS1 IDEZECZCLMOIJN-UHFFFAOYSA-N 0.000 description 2
- MSTFRUQNYRRUKZ-UHFFFAOYSA-N 5,6-dihydro-2h-thiazine Chemical compound C1CC=CNS1 MSTFRUQNYRRUKZ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- 238000000605 extraction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000004897 thiazines Chemical class 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
- SIMIXFVGSWZJJV-UHFFFAOYSA-N 1,3-thiazepine Chemical compound S1C=CC=CN=C1 SIMIXFVGSWZJJV-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
- ADZUXSOJMIFPNC-UHFFFAOYSA-N 1-[chloro(nitro)methylidene]thiazinane Chemical compound [O-][N+](=O)C(\Cl)=S1/CCCCN1 ADZUXSOJMIFPNC-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
- 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
- YPYTWPCZTGWMOZ-UHFFFAOYSA-N 2-(nitromethylidene)-1,3-thiazepane Chemical compound [O-][N+](=O)C=C1NCCCCS1 YPYTWPCZTGWMOZ-UHFFFAOYSA-N 0.000 description 1
- BROZYSIIKVFAAT-UHFFFAOYSA-N 2-[chloro(nitro)methylidene]-1,3-thiazolidine Chemical compound [O-][N+](=O)C(Cl)=C1NCCS1 BROZYSIIKVFAAT-UHFFFAOYSA-N 0.000 description 1
- OYGGLZMCYRCMCR-UHFFFAOYSA-N 2-methylsulfanyl-1,3-thiazinane Chemical compound CSC1NCCCS1 OYGGLZMCYRCMCR-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([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
- 125000004432 carbon atom Chemical group C* 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
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 239000000126 substance Substances 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- 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 |
|---|---|---|---|
| JP1135683A JPS59137473A (ja) | 1983-01-28 | 1983-01-28 | 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 |
| DE8484100712T DE3483049D1 (de) | 1983-01-28 | 1984-01-24 | Verfahren zur herstellung von einer durch nitromethylenrest substituierten heterocyclischen verbindung. |
| EP84100712A EP0115323B1 (en) | 1983-01-28 | 1984-01-24 | Process for producing heterocyclic compound having nitromethylene group as the side chain group |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1135683A JPS59137473A (ja) | 1983-01-28 | 1983-01-28 | 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 |
|---|---|
| JPS59137473A JPS59137473A (ja) | 1984-08-07 |
| JPH0373546B2 true JPH0373546B2 (pt) | 1991-11-22 |
Family
ID=11775745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1135683A Granted JPS59137473A (ja) | 1983-01-28 | 1983-01-28 | 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) | JPS59137473A (pt) |
-
1983
- 1983-01-28 JP JP1135683A patent/JPS59137473A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59137473A (ja) | 1984-08-07 |
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