JPH0341463B2 - - Google Patents
Info
- Publication number
- JPH0341463B2 JPH0341463B2 JP59178437A JP17843784A JPH0341463B2 JP H0341463 B2 JPH0341463 B2 JP H0341463B2 JP 59178437 A JP59178437 A JP 59178437A JP 17843784 A JP17843784 A JP 17843784A JP H0341463 B2 JPH0341463 B2 JP H0341463B2
- Authority
- JP
- Japan
- Prior art keywords
- nitroethylene
- nitroethane
- thio
- chloro
- acid amide
- 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 - Lifetime
Links
- -1 nitroethylene compound Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 230000002194 synthesizing effect Effects 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- FGRKPTWXGJCZMJ-UHFFFAOYSA-N n-(3-sulfanylpropyl)acetamide Chemical compound CC(=O)NCCCS FGRKPTWXGJCZMJ-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 229940080818 propionamide Drugs 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 238000002474 experimental method Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- BBYHZAMXCABVTC-UHFFFAOYSA-N n-[3-(1-chloro-2-nitroethenyl)sulfanylpropyl]acetamide Chemical group CC(=O)NCCCSC(Cl)=C[N+]([O-])=O BBYHZAMXCABVTC-UHFFFAOYSA-N 0.000 description 3
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 3
- 239000012264 purified product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SBFICQFUERLNDG-UHFFFAOYSA-N 1,1,1-trichloro-2-nitroethane Chemical group [O-][N+](=O)CC(Cl)(Cl)Cl SBFICQFUERLNDG-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-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
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000004458 analytical method Methods 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 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 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- UAYCFIUTUZHAGC-UHFFFAOYSA-N 1,1,1-tribromo-2-nitroethane Chemical compound [O-][N+](=O)CC(Br)(Br)Br UAYCFIUTUZHAGC-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
- 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
- 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
- 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
- DWYNTRJQDLLICF-UHFFFAOYSA-N 5-sulfanylpentanamide Chemical compound NC(=O)CCCCS DWYNTRJQDLLICF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- OGOLNJXUMHRHIS-UHFFFAOYSA-N N-(3-sulfanylpropyl)butanamide Chemical compound C(CCC)(=O)NCCCS OGOLNJXUMHRHIS-UHFFFAOYSA-N 0.000 description 1
- PLBUEBGPBWIDFO-UHFFFAOYSA-N N-(4-sulfanylbutyl)propanamide Chemical compound [H]C([H])C([H])([H])C(=O)N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])S PLBUEBGPBWIDFO-UHFFFAOYSA-N 0.000 description 1
- AXFZADXWLMXITO-UHFFFAOYSA-N N-acetylcysteamine Chemical compound CC(=O)NCCS AXFZADXWLMXITO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 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
- 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 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
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 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
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 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
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- VQLAUZQBHULEDZ-UHFFFAOYSA-N n-(2-sulfanylethyl)benzamide Chemical compound SCCNC(=O)C1=CC=CC=C1 VQLAUZQBHULEDZ-UHFFFAOYSA-N 0.000 description 1
- WNZWVZCUFRJIBG-UHFFFAOYSA-N n-(2-sulfanylethyl)propanamide Chemical compound CCC(=O)NCCS WNZWVZCUFRJIBG-UHFFFAOYSA-N 0.000 description 1
- JDJGNNHKOUXAKJ-UHFFFAOYSA-N n-(3-sulfanylpropyl)benzamide Chemical compound SCCCNC(=O)C1=CC=CC=C1 JDJGNNHKOUXAKJ-UHFFFAOYSA-N 0.000 description 1
- PNYWPVOENDYBJV-UHFFFAOYSA-N n-(3-sulfanylpropyl)formamide Chemical compound SCCCNC=O PNYWPVOENDYBJV-UHFFFAOYSA-N 0.000 description 1
- LNXACPPJJYUJDZ-UHFFFAOYSA-N n-(3-sulfanylpropyl)propanamide Chemical compound CCC(=O)NCCCS LNXACPPJJYUJDZ-UHFFFAOYSA-N 0.000 description 1
- VWHNZIKRYXOLMU-UHFFFAOYSA-N n-(4-sulfanylbutyl)acetamide Chemical compound CC(=O)NCCCCS VWHNZIKRYXOLMU-UHFFFAOYSA-N 0.000 description 1
- KCWIYLDXYUBKSK-UHFFFAOYSA-N n-[3-(1-chloro-2-nitroethenyl)sulfanylpropyl]benzamide Chemical group [O-][N+](=O)C=C(Cl)SCCCNC(=O)C1=CC=CC=C1 KCWIYLDXYUBKSK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17843784A JPS6157548A (ja) | 1984-08-29 | 1984-08-29 | ニトロエチレン化合物およびその合成法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17843784A JPS6157548A (ja) | 1984-08-29 | 1984-08-29 | ニトロエチレン化合物およびその合成法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6157548A JPS6157548A (ja) | 1986-03-24 |
| JPH0341463B2 true JPH0341463B2 (sk) | 1991-06-24 |
Family
ID=16048500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17843784A Granted JPS6157548A (ja) | 1984-08-29 | 1984-08-29 | ニトロエチレン化合物およびその合成法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6157548A (sk) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6061575A (ja) * | 1983-08-26 | 1985-04-09 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | 複素環式化合物の製法 |
| JPS6067473A (ja) * | 1983-08-26 | 1985-04-17 | シエル・インターナシヨネイル・リサーチ・マーチチツピイー・ベー・ウイ | 新規な農薬用複素環式化合物 |
-
1984
- 1984-08-29 JP JP17843784A patent/JPS6157548A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6061575A (ja) * | 1983-08-26 | 1985-04-09 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | 複素環式化合物の製法 |
| JPS6067473A (ja) * | 1983-08-26 | 1985-04-17 | シエル・インターナシヨネイル・リサーチ・マーチチツピイー・ベー・ウイ | 新規な農薬用複素環式化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6157548A (ja) | 1986-03-24 |
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