JPH0374222B2 - - Google Patents
Info
- Publication number
- JPH0374222B2 JPH0374222B2 JP15413083A JP15413083A JPH0374222B2 JP H0374222 B2 JPH0374222 B2 JP H0374222B2 JP 15413083 A JP15413083 A JP 15413083A JP 15413083 A JP15413083 A JP 15413083A JP H0374222 B2 JPH0374222 B2 JP H0374222B2
- Authority
- JP
- Japan
- Prior art keywords
- nitroethane
- nitromethylene
- 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
- -1 nitroethane compound Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 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 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000002585 base Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 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
- LZTIMERBDGGAJD-UHFFFAOYSA-N nithiazine Chemical compound [O-][N+](=O)C=C1NCCCS1 LZTIMERBDGGAJD-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- SBFICQFUERLNDG-UHFFFAOYSA-N 1,1,1-trichloro-2-nitroethane Chemical compound [O-][N+](=O)CC(Cl)(Cl)Cl SBFICQFUERLNDG-UHFFFAOYSA-N 0.000 description 4
- NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-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
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 4
- MLCDVZNERFBEPA-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2-nitroethane Chemical compound [O-][N+](=O)C(Cl)C(Cl)(Cl)Cl MLCDVZNERFBEPA-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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- UAYCFIUTUZHAGC-UHFFFAOYSA-N 1,1,1-tribromo-2-nitroethane Chemical compound [O-][N+](=O)CC(Br)(Br)Br UAYCFIUTUZHAGC-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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 238000007865 diluting Methods 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
- 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
- 239000007858 starting material Substances 0.000 description 2
- QPIXHCBIJQBGEJ-UHFFFAOYSA-N 1,1,1,2-tetrabromo-2-nitroethane Chemical compound [O-][N+](=O)C(Br)C(Br)(Br)Br QPIXHCBIJQBGEJ-UHFFFAOYSA-N 0.000 description 1
- ULDJYRNIWWOMGX-UHFFFAOYSA-N 1,1,1-trichloro-2-nitropropane Chemical compound [O-][N+](=O)C(C)C(Cl)(Cl)Cl ULDJYRNIWWOMGX-UHFFFAOYSA-N 0.000 description 1
- JIKDQMLRRHUBKY-UHFFFAOYSA-N 1,1,1-trifluoro-2-nitroethane Chemical compound [O-][N+](=O)CC(F)(F)F JIKDQMLRRHUBKY-UHFFFAOYSA-N 0.000 description 1
- CYCFEGJVAJFTCI-UHFFFAOYSA-N 1,1,1-triiodo-2-nitroethane Chemical compound [O-][N+](=O)CC(I)(I)I CYCFEGJVAJFTCI-UHFFFAOYSA-N 0.000 description 1
- PZOORGNLHLYCRZ-UHFFFAOYSA-N 1,1,2-tribromo-1-chloro-2-nitroethane Chemical compound [O-][N+](=O)C(Br)C(Cl)(Br)Br PZOORGNLHLYCRZ-UHFFFAOYSA-N 0.000 description 1
- VUZZLXDACQGJKM-UHFFFAOYSA-N 1,1-dibromo-1,2-dichloro-2-nitroethane Chemical compound [O-][N+](=O)C(Cl)C(Cl)(Br)Br VUZZLXDACQGJKM-UHFFFAOYSA-N 0.000 description 1
- XKNLISXRJGRTGP-UHFFFAOYSA-N 1,1-dibromo-1-chloro-2-nitroethane Chemical compound [O-][N+](=O)CC(Cl)(Br)Br XKNLISXRJGRTGP-UHFFFAOYSA-N 0.000 description 1
- WKCCUOQFFSDOLW-UHFFFAOYSA-N 1,1-dibromo-1-fluoro-2-nitroethane Chemical compound [O-][N+](=O)CC(F)(Br)Br WKCCUOQFFSDOLW-UHFFFAOYSA-N 0.000 description 1
- SSNFRFXOBODOFS-UHFFFAOYSA-N 1,1-dibromo-1-iodo-2-nitroethane Chemical compound [O-][N+](=O)CC(Br)(Br)I SSNFRFXOBODOFS-UHFFFAOYSA-N 0.000 description 1
- MGCUWGNNQFAYIV-UHFFFAOYSA-N 1,1-dichloro-1-fluoro-2-nitroethane Chemical compound [O-][N+](=O)CC(F)(Cl)Cl MGCUWGNNQFAYIV-UHFFFAOYSA-N 0.000 description 1
- BHLAZNKHRYTFAN-UHFFFAOYSA-N 1,1-dichloro-1-iodo-2-nitroethane Chemical compound [O-][N+](=O)CC(Cl)(Cl)I BHLAZNKHRYTFAN-UHFFFAOYSA-N 0.000 description 1
- YABMEZKQFRPQNY-UHFFFAOYSA-N 1,2-dibromo-1,1-dichloro-2-nitroethane Chemical compound [O-][N+](=O)C(Br)C(Cl)(Cl)Br YABMEZKQFRPQNY-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
- ONTZYYWACSMBPU-UHFFFAOYSA-N 1-(nitromethylidene)-2H-1,3-thiazine Chemical compound [N+](=O)([O-])C=S1CN=CC=C1 ONTZYYWACSMBPU-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
- BGUOLBQHFMMZQU-UHFFFAOYSA-N 1-bromo-1,1,2-trichloro-2-nitroethane Chemical compound [O-][N+](=O)C(Cl)C(Cl)(Cl)Br BGUOLBQHFMMZQU-UHFFFAOYSA-N 0.000 description 1
- QEBIIPWZIWCBMR-UHFFFAOYSA-N 1-bromo-1,1-dichloro-2-nitroethane Chemical compound [O-][N+](=O)CC(Cl)(Cl)Br QEBIIPWZIWCBMR-UHFFFAOYSA-N 0.000 description 1
- LIBXTYGCRZBBGJ-UHFFFAOYSA-N 1-bromo-1,1-dichloro-2-nitropropane Chemical compound [O-][N+](=O)C(C)C(Cl)(Cl)Br LIBXTYGCRZBBGJ-UHFFFAOYSA-N 0.000 description 1
- QJNWUELUMBXENX-UHFFFAOYSA-N 1-bromo-1,1-difluoro-2-nitroethane Chemical compound [O-][N+](=O)CC(F)(F)Br QJNWUELUMBXENX-UHFFFAOYSA-N 0.000 description 1
- SFUSLXDJHBGXTK-UHFFFAOYSA-N 1-bromo-1,1-diiodo-2-nitroethane Chemical compound [O-][N+](=O)CC(Br)(I)I SFUSLXDJHBGXTK-UHFFFAOYSA-N 0.000 description 1
- HBNGFHGVRANAEJ-UHFFFAOYSA-N 1-chloro-1,1-difluoro-2-nitroethane Chemical compound [O-][N+](=O)CC(F)(F)Cl HBNGFHGVRANAEJ-UHFFFAOYSA-N 0.000 description 1
- DDVMHDMYDKXPGZ-UHFFFAOYSA-N 1-chloro-1,1-diiodo-2-nitroethane Chemical compound [O-][N+](=O)CC(Cl)(I)I DDVMHDMYDKXPGZ-UHFFFAOYSA-N 0.000 description 1
- YPYTWPCZTGWMOZ-UHFFFAOYSA-N 2-(nitromethylidene)-1,3-thiazepane Chemical class [O-][N+](=O)C=C1NCCCCS1 YPYTWPCZTGWMOZ-UHFFFAOYSA-N 0.000 description 1
- HMIVOGBWFCNJNI-UHFFFAOYSA-N 2-[chloro(nitro)methylidene]-1,3-thiazepane Chemical compound [O-][N+](=O)C(Cl)=C1NCCCCS1 HMIVOGBWFCNJNI-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
- VFHKWDMNJOITOV-UHFFFAOYSA-N 2-bromo-1,1,1-trichloro-2-nitroethane Chemical compound [O-][N+](=O)C(Br)C(Cl)(Cl)Cl VFHKWDMNJOITOV-UHFFFAOYSA-N 0.000 description 1
- OYGGLZMCYRCMCR-UHFFFAOYSA-N 2-methylsulfanyl-1,3-thiazinane Chemical compound CSC1NCCCS1 OYGGLZMCYRCMCR-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
- 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
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- GXGKSRMHXKQEQC-UHFFFAOYSA-N [N]CC[N] Chemical compound [N]CC[N] GXGKSRMHXKQEQC-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
- 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
- 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
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetroxide Inorganic materials [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-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
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NYERMPLPURRVGM-UHFFFAOYSA-N thiazepine Chemical compound S1C=CC=CC=N1 NYERMPLPURRVGM-UHFFFAOYSA-N 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 150000003548 thiazolidines Chemical class 0.000 description 1
Landscapes
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15413083A JPS6048978A (ja) | 1983-08-25 | 1983-08-25 | 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 |
| US06/639,919 US4625025A (en) | 1983-08-25 | 1984-08-10 | Process for producing a 2H-1,3-thiazolidine, 2H-tetrahydro-1,3-thiazine, or 2H-hexahydro-1,3-thiazepine derivative substituted at the 2 position by a nitromethylene group derivative |
| KR1019840004929A KR860002191B1 (ko) | 1983-08-25 | 1984-08-16 | 측쇄기로서 니트로메틸렌기를 갖는 헤테로고리 화합물을 제조하는 방법 |
| DE8484110010T DE3484038D1 (de) | 1983-08-25 | 1984-08-22 | Verfahren zur herstellung einer heterocyclischen verbindung mit einer nitromethylengruppe als seitenkette. |
| EP84110010A EP0135803B1 (en) | 1983-08-25 | 1984-08-22 | Process for producing heterocyclic compounds having nitromethylene group as the side chain group |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15413083A JPS6048978A (ja) | 1983-08-25 | 1983-08-25 | 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 |
|---|---|
| JPS6048978A JPS6048978A (ja) | 1985-03-16 |
| JPH0374222B2 true JPH0374222B2 (enrdf_load_stackoverflow) | 1991-11-26 |
Family
ID=15577553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15413083A Granted JPS6048978A (ja) | 1983-08-25 | 1983-08-25 | 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) | JPS6048978A (enrdf_load_stackoverflow) |
-
1983
- 1983-08-25 JP JP15413083A patent/JPS6048978A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6048978A (ja) | 1985-03-16 |
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