SE500292C2 - 2-bensyltio-1-cykloalken-1-karboxamider och deras sulfoxider, sätt för deras framställning och deras användning för syntes av tri- och 4,5-tetrametylen-4-isotiazolin-3-oner - Google Patents
2-bensyltio-1-cykloalken-1-karboxamider och deras sulfoxider, sätt för deras framställning och deras användning för syntes av tri- och 4,5-tetrametylen-4-isotiazolin-3-onerInfo
- Publication number
- SE500292C2 SE500292C2 SE8602523A SE8602523A SE500292C2 SE 500292 C2 SE500292 C2 SE 500292C2 SE 8602523 A SE8602523 A SE 8602523A SE 8602523 A SE8602523 A SE 8602523A SE 500292 C2 SE500292 C2 SE 500292C2
- Authority
- SE
- Sweden
- Prior art keywords
- cyclopentene
- carboxamide
- benzylthio
- formula
- isothiazolin
- Prior art date
Links
- 150000003462 sulfoxides Chemical class 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 26
- 230000015572 biosynthetic process Effects 0.000 title description 4
- 238000003786 synthesis reaction Methods 0.000 title description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 55
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 51
- 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 claims abstract description 16
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 4
- 239000011707 mineral Substances 0.000 claims abstract description 4
- 150000007530 organic bases Chemical class 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 239000012458 free base Substances 0.000 claims abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 183
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 39
- 238000003756 stirring Methods 0.000 claims description 38
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 28
- -1 isopropyl- Chemical group 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- CGRBZLXKUCYOAC-UHFFFAOYSA-N 2-benzylsulfanylcyclopentene-1-carboxamide Chemical compound C1CCC(C(=O)N)=C1SCC1=CC=CC=C1 CGRBZLXKUCYOAC-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 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 claims description 3
- 150000003573 thiols Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
- 239000000203 mixture Substances 0.000 description 44
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- 238000006243 chemical reaction Methods 0.000 description 22
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- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 150000003568 thioethers Chemical class 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 9
- NLABIJAJRNLCLZ-UHFFFAOYSA-N 2-benzylsulfanylcyclopentene-1-carboxylic acid Chemical compound C1CCC(C(=O)O)=C1SCC1=CC=CC=C1 NLABIJAJRNLCLZ-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
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- 239000007858 starting material Substances 0.000 description 3
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229940035339 tri-chlor Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Detergent Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8508469A FR2583046B1 (fr) | 1985-06-05 | 1985-06-05 | Alkyl ou aralkyl thio-2 cycloalkene-1 carboxamides-1 et leurs sulfoxydes, leurs procedes de preparation et leur application a la synthese de tri et tetramethylene-4,5 isothiazoline-4, ones-3 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8602523D0 SE8602523D0 (sv) | 1986-06-04 |
| SE8602523L SE8602523L (sv) | 1986-12-06 |
| SE500292C2 true SE500292C2 (sv) | 1994-05-30 |
Family
ID=9319887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8602523A SE500292C2 (sv) | 1985-06-05 | 1986-06-04 | 2-bensyltio-1-cykloalken-1-karboxamider och deras sulfoxider, sätt för deras framställning och deras användning för syntes av tri- och 4,5-tetrametylen-4-isotiazolin-3-oner |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4851541A (fi) |
| JP (2) | JPS61293963A (fi) |
| BE (1) | BE904879A (fi) |
| CA (1) | CA1265146A (fi) |
| CH (1) | CH671575A5 (fi) |
| DE (1) | DE3618711A1 (fi) |
| DK (1) | DK263886A (fi) |
| FI (1) | FI86057C (fi) |
| FR (1) | FR2583046B1 (fi) |
| GB (1) | GB2176187B (fi) |
| IT (1) | IT1190042B (fi) |
| NL (1) | NL193614C (fi) |
| SE (1) | SE500292C2 (fi) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8921221D0 (en) * | 1989-09-20 | 1989-11-08 | Ici Plc | Compound,preparation and use |
| GB8921220D0 (en) * | 1989-09-20 | 1989-11-08 | Ici Plc | Process |
| GB9020924D0 (en) * | 1990-09-26 | 1990-11-07 | Ici Plc | Compound,use and preparation |
| GB9020933D0 (en) * | 1990-09-26 | 1990-11-07 | Ici Plc | Compound,preparation and use |
| US5373016A (en) * | 1993-05-28 | 1994-12-13 | Zeneca, Inc. | Protection of isothiazolinone biocides from free radicals |
| TW402585B (en) * | 1993-11-24 | 2000-08-21 | Sumitomo Chemical Co | Method for producing alkylsulfinylbenzamides and 1, 2-benzisothiazol-3-ones |
| US6576792B2 (en) | 2001-05-04 | 2003-06-10 | Eastman Kodak Company | 2-halo-1-cycloalkenecarboxamides and their preparation |
| US10120000B2 (en) * | 2015-07-15 | 2018-11-06 | Oracle International Corporation | On-chip current sensing employing power distribution network voltage de-convolution |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2767172A (en) * | 1954-12-29 | 1956-10-16 | Schenley Ind Inc | Process for the production of n-benzylidene and n-quinolylmethylene-substituted 2-aminobenz-isothiazolones |
| US3012039A (en) * | 1958-03-14 | 1961-12-05 | Ici Ltd | 2-p-chlorobenzyl-1, 2-benzisothiazolone |
| CH395094A (de) * | 1960-03-24 | 1965-07-15 | Wander Ag Dr A | Verfahren zur Herstellung von 6-Chlor-benzisothiazolon |
| DE1147947B (de) * | 1961-07-25 | 1963-05-02 | Knoll Ag | Verfahren zur Herstellung neuer 1, 2-Benzisothiazolone |
| US3362992A (en) * | 1965-05-27 | 1968-01-09 | Schwartz Herbert | Novel cycloalkenecarboxanilides |
| US3661974A (en) * | 1970-04-27 | 1972-05-09 | Sherwin Williams Co | 2-carbalkoxy-phenyl sulfenamides |
| EP0000254B1 (en) * | 1977-06-20 | 1981-06-10 | Beecham Group Plc | Antithrombotic 2-(gamma-(1-piperidinyl)propyl)1,2-benzisothiazol 3-one, its pharmaceutically acceptable acid addition salts, their preparation and their compositions |
| FR2492376A1 (fr) * | 1980-10-17 | 1982-04-23 | Cird | Polymethylene-4,5 isothiazoline-4 ones-3, leur procede de preparation et leurs utilisation comme agents bactericides et fongicides |
| JPS58177982A (ja) * | 1982-04-09 | 1983-10-18 | Green Cross Corp:The | ベンズイソチアゾリン誘導体及び抗白癬菌剤 |
-
1985
- 1985-06-05 FR FR8508469A patent/FR2583046B1/fr not_active Expired
-
1986
- 1986-06-04 CH CH2261/86A patent/CH671575A5/fr not_active IP Right Cessation
- 1986-06-04 FI FI862386A patent/FI86057C/fi not_active IP Right Cessation
- 1986-06-04 JP JP61131042A patent/JPS61293963A/ja active Granted
- 1986-06-04 CA CA000510846A patent/CA1265146A/fr not_active Expired - Lifetime
- 1986-06-04 NL NL8601443A patent/NL193614C/nl not_active IP Right Cessation
- 1986-06-04 DE DE19863618711 patent/DE3618711A1/de active Granted
- 1986-06-04 DK DK263886A patent/DK263886A/da not_active Application Discontinuation
- 1986-06-04 SE SE8602523A patent/SE500292C2/sv not_active IP Right Cessation
- 1986-06-05 BE BE0/216748A patent/BE904879A/fr not_active IP Right Cessation
- 1986-06-05 IT IT20690/86A patent/IT1190042B/it active
- 1986-06-05 GB GB08613653A patent/GB2176187B/en not_active Expired
- 1986-06-05 US US06/870,903 patent/US4851541A/en not_active Expired - Lifetime
-
1991
- 1991-02-21 JP JP3027582A patent/JPH04210957A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FI862386A (fi) | 1986-12-06 |
| NL8601443A (nl) | 1987-01-02 |
| SE8602523D0 (sv) | 1986-06-04 |
| CH671575A5 (fi) | 1989-09-15 |
| DK263886D0 (da) | 1986-06-04 |
| JPH04210957A (ja) | 1992-08-03 |
| DE3618711A1 (de) | 1986-12-11 |
| GB2176187B (en) | 1988-12-29 |
| DK263886A (da) | 1986-12-06 |
| CA1265146A (fr) | 1990-01-30 |
| NL193614C (nl) | 2000-04-04 |
| IT8620690A1 (it) | 1987-12-05 |
| GB2176187A (en) | 1986-12-17 |
| US4851541A (en) | 1989-07-25 |
| GB8613653D0 (en) | 1986-07-09 |
| SE8602523L (sv) | 1986-12-06 |
| NL193614B (nl) | 1999-12-01 |
| FR2583046B1 (fr) | 1987-07-17 |
| JPS61293963A (ja) | 1986-12-24 |
| JPH0473B2 (fi) | 1992-01-06 |
| FI86057B (fi) | 1992-03-31 |
| FR2583046A1 (fr) | 1986-12-12 |
| JPH0565505B2 (fi) | 1993-09-17 |
| FI86057C (fi) | 1992-07-10 |
| IT1190042B (it) | 1988-02-10 |
| BE904879A (fr) | 1986-12-05 |
| DE3618711C2 (fi) | 1992-02-06 |
| FI862386A0 (fi) | 1986-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |