CS196424B2 - Method of producing 2-hydroxy benzothiazole - Google Patents
Method of producing 2-hydroxy benzothiazole Download PDFInfo
- Publication number
- CS196424B2 CS196424B2 CS781880A CS188078A CS196424B2 CS 196424 B2 CS196424 B2 CS 196424B2 CS 781880 A CS781880 A CS 781880A CS 188078 A CS188078 A CS 188078A CS 196424 B2 CS196424 B2 CS 196424B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- solvent
- carbonyl sulfide
- mixture
- room temperature
- solution
- Prior art date
Links
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 5
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims 2
- 230000004048 modification Effects 0.000 claims 2
- 239000000155 melt Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 abstract description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- -1 aliphatic alcohols Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000008635 plant growth Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZCXGMSGCBDSEOY-UHFFFAOYSA-N 2-benzothiazolsulfonic acid Chemical compound C1=CC=C2SC(S(=O)(=O)O)=NC2=C1 ZCXGMSGCBDSEOY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/782,126 US4150027A (en) | 1977-03-28 | 1977-03-28 | Process for preparing 2-hydroxybenzothiazole compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196424B2 true CS196424B2 (en) | 1980-03-31 |
Family
ID=25125054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS781880A CS196424B2 (en) | 1977-03-28 | 1978-03-24 | Method of producing 2-hydroxy benzothiazole |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4150027A (pl) |
| JP (1) | JPS53119871A (pl) |
| AR (1) | AR222011A1 (pl) |
| AU (1) | AU514563B2 (pl) |
| BE (1) | BE865297A (pl) |
| BG (1) | BG29872A3 (pl) |
| BR (1) | BR7801832A (pl) |
| CA (1) | CA1094081A (pl) |
| CH (1) | CH634838A5 (pl) |
| CS (1) | CS196424B2 (pl) |
| DD (1) | DD135384A5 (pl) |
| DE (1) | DE2812940A1 (pl) |
| FR (1) | FR2385706A1 (pl) |
| GB (1) | GB1576307A (pl) |
| IL (1) | IL54355A (pl) |
| IT (1) | IT1096154B (pl) |
| MX (1) | MX5290E (pl) |
| MY (1) | MY8200123A (pl) |
| NL (1) | NL7803144A (pl) |
| PH (1) | PH13026A (pl) |
| PL (1) | PL110436B1 (pl) |
| SU (1) | SU670220A3 (pl) |
| YU (1) | YU71178A (pl) |
| ZA (1) | ZA781734B (pl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3017153A1 (de) * | 1980-05-05 | 1981-11-12 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von 2-hydroxybenzthiazolen |
| UA51621C2 (uk) * | 1995-12-21 | 2002-12-16 | Новартіс Аг | Похідні 3-аміно-2-меркаптобензойної кислоти та способи їх одержання |
| CN108101863B (zh) * | 2017-12-12 | 2022-01-25 | 内蒙古工业大学 | 一种以羰基硫与二硫化物为原料合成苯并噻唑-2-酮类衍生物的方法 |
| CN115057828A (zh) * | 2022-08-15 | 2022-09-16 | 湖南速博生物技术有限公司 | 一种苯并噁唑酮的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857392A (en) * | 1958-10-21 | Certificate of correction | ||
| US2915525A (en) * | 1957-03-18 | 1959-12-01 | Monsanto Chemicals | Preparation of arylenebenzoxazolols and arylenebenzothiazolols |
-
1977
- 1977-03-28 US US05/782,126 patent/US4150027A/en not_active Expired - Lifetime
-
1978
- 1978-03-22 PH PH20919A patent/PH13026A/en unknown
- 1978-03-23 CA CA299,659A patent/CA1094081A/en not_active Expired
- 1978-03-23 AU AU34477/78A patent/AU514563B2/en not_active Expired
- 1978-03-23 CH CH319378A patent/CH634838A5/de not_active IP Right Cessation
- 1978-03-23 NL NL7803144A patent/NL7803144A/xx not_active Application Discontinuation
- 1978-03-23 DE DE19782812940 patent/DE2812940A1/de not_active Withdrawn
- 1978-03-24 BE BE186253A patent/BE865297A/xx not_active IP Right Cessation
- 1978-03-24 IT IT21622/78A patent/IT1096154B/it active
- 1978-03-24 CS CS781880A patent/CS196424B2/cs unknown
- 1978-03-24 FR FR7808793A patent/FR2385706A1/fr active Granted
- 1978-03-25 PL PL1978205590A patent/PL110436B1/pl unknown
- 1978-03-27 YU YU00711/78A patent/YU71178A/xx unknown
- 1978-03-27 SU SU782594800A patent/SU670220A3/ru active
- 1978-03-27 DD DD78204420A patent/DD135384A5/xx unknown
- 1978-03-27 IL IL54355A patent/IL54355A/xx unknown
- 1978-03-27 BR BR7801832A patent/BR7801832A/pt unknown
- 1978-03-27 MX MX786949U patent/MX5290E/es unknown
- 1978-03-27 JP JP3427078A patent/JPS53119871A/ja active Pending
- 1978-03-27 BG BG039181A patent/BG29872A3/xx unknown
- 1978-03-27 AR AR271546A patent/AR222011A1/es active
- 1978-03-28 ZA ZA00781734A patent/ZA781734B/xx unknown
- 1978-03-28 GB GB11952/78A patent/GB1576307A/en not_active Expired
-
1982
- 1982-12-30 MY MY123/82A patent/MY8200123A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU514563B2 (en) | 1981-02-19 |
| JPS53119871A (en) | 1978-10-19 |
| BE865297A (fr) | 1978-09-25 |
| SU670220A3 (ru) | 1979-06-25 |
| AR222011A1 (es) | 1981-04-15 |
| PL205590A1 (pl) | 1979-03-12 |
| NL7803144A (nl) | 1978-10-02 |
| CA1094081A (en) | 1981-01-20 |
| PL110436B1 (en) | 1980-07-31 |
| YU71178A (en) | 1983-01-21 |
| DD135384A5 (de) | 1979-05-02 |
| BR7801832A (pt) | 1978-12-19 |
| IT7821622A0 (it) | 1978-03-24 |
| MX5290E (es) | 1983-06-06 |
| ZA781734B (en) | 1979-03-28 |
| DE2812940A1 (de) | 1978-10-12 |
| IL54355A (en) | 1981-06-29 |
| IL54355A0 (en) | 1978-06-15 |
| IT1096154B (it) | 1985-08-17 |
| AU3447778A (en) | 1979-09-27 |
| US4150027A (en) | 1979-04-17 |
| GB1576307A (en) | 1980-10-08 |
| MY8200123A (en) | 1982-12-31 |
| CH634838A5 (de) | 1983-02-28 |
| FR2385706B1 (pl) | 1983-01-21 |
| BG29872A3 (en) | 1981-02-16 |
| PH13026A (en) | 1979-11-15 |
| FR2385706A1 (fr) | 1978-10-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3725427A (en) | Certain 2,4-dimethyl-5-carboxamido-thiazoles | |
| JPH0469388A (ja) | （６，７―置換―８―アルコキシ―１―シクロプロピル―１，４―ジヒドロ―４―オキソ―３―キノリンカルボン酸―ｏ↑３，ｏ↑４）ビス（アシルオキシ―ｏ）ホウ素化合物及びその塩並びにその製造方法 | |
| JP4217924B2 (ja) | ３−アミノ−２−メルカプト安息香酸誘導体及びその製造方法 | |
| EP0645355B1 (de) | Verfahren zur Herstellung von Trifluorethylschwefelverbindungen aus Thiolaten und 1-Chlor-2,2,2-trifluorethan | |
| CS196424B2 (en) | Method of producing 2-hydroxy benzothiazole | |
| US2895992A (en) | Process for the production of benzoic | |
| US5084456A (en) | Oxazolopyridine compounds | |
| KR0130975B1 (ko) | 제초제로서 유용한 o-카르복시아릴이미다졸리논 화합물의 제조방법 | |
| US3794636A (en) | Process for preparation of thiazole hydrohalides | |
| US1999432A (en) | Production of aminoalkyl sulphonic acids | |
| US4925944A (en) | Process for the preparation of o-carboxypyridyl- and o-carboxyquinolylimidazolinones | |
| SU764609A3 (ru) | Способ получени производных бензимидазолкарбамата | |
| JPS6094979A (ja) | １，２，３−トリチアン誘導体の新規製造法 | |
| CA1038870A (en) | Pyrimidine derivatives | |
| KR800001548B1 (ko) | 2-하이드록시 벤조티아졸의 제조방법 | |
| US2652401A (en) | Benzothiazole derivatives and method of production | |
| US2772279A (en) | Preparation of sulfenamides | |
| US2179984A (en) | Process fob the manufacture of | |
| US2293465A (en) | Process for the manufacture of mercaptothiazolines | |
| US2886584A (en) | Cyano substituted aliphatic isothiocyanates | |
| US3647813A (en) | Process for the manufacture of benzoxazolone-6-beta-hydroxy-ethyl-sulfone | |
| KR860000671B1 (ko) | 퀴놀린 카르복실산의 피페라지닐 유도체의 제조 방법 | |
| Mizuno et al. | Benzothiazoles. XII.: Studies on Reaction between 2-Chlorobenzothiazoles and Compounds possessing Reactive Methylene Groups. | |
| US2692881A (en) | Benzothiazole derivatives | |
| US3063988A (en) | Steroid-21-amino acid esters and process of preparing them |