JPS5942376A - チオフエン系化合物及びその製造法 - Google Patents
チオフエン系化合物及びその製造法Info
- Publication number
- JPS5942376A JPS5942376A JP15169482A JP15169482A JPS5942376A JP S5942376 A JPS5942376 A JP S5942376A JP 15169482 A JP15169482 A JP 15169482A JP 15169482 A JP15169482 A JP 15169482A JP S5942376 A JPS5942376 A JP S5942376A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- parts
- lower alkyl
- compound represented
- 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.)
- Granted
Links
- -1 Thiophene compound Chemical class 0.000 title claims description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims description 10
- 229930192474 thiophene Natural products 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 12
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- 239000000987 azo dye Substances 0.000 abstract description 2
- 230000005494 condensation Effects 0.000 abstract description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 2
- 230000000802 nitrating effect Effects 0.000 abstract description 2
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000005457 ice water Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 150000001409 amidines Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- JIZRGGUCOQKGQD-UHFFFAOYSA-N 2-nitrothiophene Chemical class [O-][N+](=O)C1=CC=CS1 JIZRGGUCOQKGQD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 3
- IGKMJWPWSFSLDV-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-diene-1-carbaldehyde Chemical compound CC1=CCC(C)(C=O)C=C1 IGKMJWPWSFSLDV-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- UAYKGOMDUQLCJS-UHFFFAOYSA-N ethylsulfanyl acetate Chemical compound CCSOC(C)=O UAYKGOMDUQLCJS-UHFFFAOYSA-N 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- HXJGXEAQCSIDLS-UHFFFAOYSA-N 2-iminothiolane-3-carbonitrile Chemical compound N=C1SCCC1C#N HXJGXEAQCSIDLS-UHFFFAOYSA-N 0.000 description 1
- YDLAHBBJAGGIJZ-UHFFFAOYSA-N 2-sulfanylethyl acetate Chemical compound CC(=O)OCCS YDLAHBBJAGGIJZ-UHFFFAOYSA-N 0.000 description 1
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 1
- PSRZQUKEUSRHJJ-UHFFFAOYSA-N 5-nitrothiophen-2-amine Chemical class NC1=CC=C([N+]([O-])=O)S1 PSRZQUKEUSRHJJ-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- AVMNFQHJOOYCAP-UHFFFAOYSA-N acetic acid;propanoic acid Chemical compound CC(O)=O.CCC(O)=O AVMNFQHJOOYCAP-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- ANGDWNBGPBMQHW-UHFFFAOYSA-N methyl cyanoacetate Chemical compound COC(=O)CC#N ANGDWNBGPBMQHW-UHFFFAOYSA-N 0.000 description 1
- SQICNHICBKAAHF-UHFFFAOYSA-N n-thiophen-2-ylformamide Chemical class O=CNC1=CC=CS1 SQICNHICBKAAHF-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15169482A JPS5942376A (ja) | 1982-09-02 | 1982-09-02 | チオフエン系化合物及びその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15169482A JPS5942376A (ja) | 1982-09-02 | 1982-09-02 | チオフエン系化合物及びその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5942376A true JPS5942376A (ja) | 1984-03-08 |
| JPH03393B2 JPH03393B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-01-07 |
Family
ID=15524217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15169482A Granted JPS5942376A (ja) | 1982-09-02 | 1982-09-02 | チオフエン系化合物及びその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5942376A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61212579A (ja) * | 1985-03-02 | 1986-09-20 | バスフ アクチェン ゲゼルシャフト | チオフエン誘導体 |
| US4837269A (en) * | 1986-07-03 | 1989-06-06 | Basf Aktiengesellschaft | 2-aminothiophene radical substituted by an electron withdrawing group |
| US5206375A (en) * | 1985-03-02 | 1993-04-27 | Basf Aktiengesellschaft | Thiophene derivatives |
| US5679800A (en) * | 1984-08-30 | 1997-10-21 | Clariant Finance (Bvi) Limited | 2-Amino-3,5,disubstituted-4-halothiophenes and processes for the synthesis thereof |
-
1982
- 1982-09-02 JP JP15169482A patent/JPS5942376A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5679800A (en) * | 1984-08-30 | 1997-10-21 | Clariant Finance (Bvi) Limited | 2-Amino-3,5,disubstituted-4-halothiophenes and processes for the synthesis thereof |
| JPS61212579A (ja) * | 1985-03-02 | 1986-09-20 | バスフ アクチェン ゲゼルシャフト | チオフエン誘導体 |
| US5206375A (en) * | 1985-03-02 | 1993-04-27 | Basf Aktiengesellschaft | Thiophene derivatives |
| US4837269A (en) * | 1986-07-03 | 1989-06-06 | Basf Aktiengesellschaft | 2-aminothiophene radical substituted by an electron withdrawing group |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03393B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-01-07 |
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