JPS6246544B2 - - Google Patents
Info
- Publication number
- JPS6246544B2 JPS6246544B2 JP2727185A JP2727185A JPS6246544B2 JP S6246544 B2 JPS6246544 B2 JP S6246544B2 JP 2727185 A JP2727185 A JP 2727185A JP 2727185 A JP2727185 A JP 2727185A JP S6246544 B2 JPS6246544 B2 JP S6246544B2
- Authority
- JP
- Japan
- Prior art keywords
- benzothiazole
- group
- reaction
- formula
- general formula
- 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
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- -1 N-substituted amino group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 15
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- AMWVFOHECZHTQT-UHFFFAOYSA-N 2-(2-methylphenyl)-1,3-benzothiazole Chemical compound CC1=CC=CC=C1C1=NC2=CC=CC=C2S1 AMWVFOHECZHTQT-UHFFFAOYSA-N 0.000 description 2
- YCAIAEVWVDGLAV-UHFFFAOYSA-N 2-tert-butyl-1,3-benzothiazole Chemical compound C1=CC=C2SC(C(C)(C)C)=NC2=C1 YCAIAEVWVDGLAV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- OFPLWAOEAHGPCV-UHFFFAOYSA-N 2-(1,3-thiazol-2-yl)-1,3-benzothiazole Chemical compound C1=CSC(C=2SC3=CC=CC=C3N=2)=N1 OFPLWAOEAHGPCV-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- KVYZTLUBKLUONP-UHFFFAOYSA-N 2-(2-chlorophenyl)-1,3-benzothiazole Chemical compound ClC1=CC=CC=C1C1=NC2=CC=CC=C2S1 KVYZTLUBKLUONP-UHFFFAOYSA-N 0.000 description 1
- PYOHHBLCCRIMFM-UHFFFAOYSA-N 2-(furan-2-yl)-1,3-benzothiazole Chemical compound C1=COC(C=2SC3=CC=CC=C3N=2)=C1 PYOHHBLCCRIMFM-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- XSWCYXIBEZMXMM-UHFFFAOYSA-N 2-pyridin-2-yl-1,3-benzothiazole Chemical compound N1=CC=CC=C1C1=NC2=CC=CC=C2S1 XSWCYXIBEZMXMM-UHFFFAOYSA-N 0.000 description 1
- LQTLGGKCYQGOGU-UHFFFAOYSA-N C(C(C)(C)C)#N.CC(C#N)(C)C Chemical compound C(C(C)(C)C)#N.CC(C#N)(C)C LQTLGGKCYQGOGU-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- YRPHDKJGFSDFJF-UHFFFAOYSA-N O1C(=CC=C1)C#N.O1C(=CC=C1)C#N Chemical compound O1C(=CC=C1)C#N.O1C(=CC=C1)C#N YRPHDKJGFSDFJF-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia 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
- 238000009835 boiling Methods 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 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
- 230000001766 physiological effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-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
- PBEXQBWLOXMXCU-UHFFFAOYSA-N pyridine-3-carbonitrile Chemical compound N#CC1=CC=CN=C1.N#CC1=CC=CN=C1 PBEXQBWLOXMXCU-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2727185A JPS61186372A (ja) | 1985-02-14 | 1985-02-14 | ベンゾチアゾ−ルの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2727185A JPS61186372A (ja) | 1985-02-14 | 1985-02-14 | ベンゾチアゾ−ルの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61186372A JPS61186372A (ja) | 1986-08-20 |
| JPS6246544B2 true JPS6246544B2 (enrdf_load_html_response) | 1987-10-02 |
Family
ID=12216410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2727185A Granted JPS61186372A (ja) | 1985-02-14 | 1985-02-14 | ベンゾチアゾ−ルの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61186372A (enrdf_load_html_response) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04242622A (ja) * | 1990-12-25 | 1992-08-31 | Haruo Miyata | ソファー、カーテンなどの洗浄装置 |
| WO1998041991A1 (fr) * | 1997-03-17 | 1998-09-24 | Hitachi, Ltd. | Procede d'exploitation d'un reacteur |
| CN104910098B (zh) * | 2015-06-02 | 2017-03-22 | 大连理工大学 | 一种2‑芳基苯并噻唑类化合物的合成方法 |
-
1985
- 1985-02-14 JP JP2727185A patent/JPS61186372A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61186372A (ja) | 1986-08-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |