DE2237080A1 - Benzothiazolderivate - Google Patents
BenzothiazolderivateInfo
- Publication number
- DE2237080A1 DE2237080A1 DE2237080A DE2237080A DE2237080A1 DE 2237080 A1 DE2237080 A1 DE 2237080A1 DE 2237080 A DE2237080 A DE 2237080A DE 2237080 A DE2237080 A DE 2237080A DE 2237080 A1 DE2237080 A1 DE 2237080A1
- Authority
- DE
- Germany
- Prior art keywords
- benzothiazole
- hydroxyphenyl
- phthalimide
- mixture
- compounds
- 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.)
- Pending
Links
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 15
- MVVGSPCXHRFDDR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2S1 MVVGSPCXHRFDDR-UHFFFAOYSA-N 0.000 claims description 10
- MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical compound C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 claims description 7
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- -1 2-hydroxyphenyl Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- GHGZVWOTJDLREY-UHFFFAOYSA-N 2-(1,3-benzoxazol-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2O1 GHGZVWOTJDLREY-UHFFFAOYSA-N 0.000 description 1
- DPSZRUWAYGVAQB-UHFFFAOYSA-N 2-[[3-(1,3-benzothiazol-2-yl)-4-hydroxyphenyl]methyl]isoindole-1,3-dione Chemical compound OC1=C(C=C(C=C1)CN1C(C=2C(C1=O)=CC=CC2)=O)C=2SC1=C(N2)C=CC=C1 DPSZRUWAYGVAQB-UHFFFAOYSA-N 0.000 description 1
- FRERDVKYFXHCHL-UHFFFAOYSA-N [P].OC1=C(C=CC=C1)C=1SC2=C(N1)C=CC=C2 Chemical compound [P].OC1=C(C=CC=C1)C=1SC2=C(N1)C=CC=C2 FRERDVKYFXHCHL-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- XWXMGTIHBYFTIE-UHFFFAOYSA-N chembl203360 Chemical compound OC1=CC=CC=C1C1=NC2=CC=CC=C2N1 XWXMGTIHBYFTIE-UHFFFAOYSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Luminescent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16783871A | 1971-07-30 | 1971-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2237080A1 true DE2237080A1 (de) | 1973-02-08 |
Family
ID=22609048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2237080A Pending DE2237080A1 (de) | 1971-07-30 | 1972-07-28 | Benzothiazolderivate |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3723449A (enExample) |
| JP (2) | JPS4825027A (enExample) |
| BE (1) | BE786758A (enExample) |
| CA (1) | CA990300A (enExample) |
| DE (1) | DE2237080A1 (enExample) |
| FR (1) | FR2149129A5 (enExample) |
| GB (1) | GB1339373A (enExample) |
| NL (1) | NL7210317A (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4039553A (en) * | 1974-02-22 | 1977-08-02 | Gaf Corporation | Certain 2(2'-hydroxyphenyl)benzothiazolo derivatives |
| US3995157A (en) * | 1975-02-18 | 1976-11-30 | General Electric Company | Surface flaw detection |
| DE3544627A1 (de) * | 1985-12-17 | 1987-06-19 | Rodenstock Optik G | Brillenglas aus einem kunststoffmaterial mit einer fluoreszierenden markierung |
| FR2766821A1 (fr) * | 1997-07-29 | 1999-02-05 | Sanofi Sa | Derives de 1,3-oxazolinyl-biphenyle, leur procede de preparation et leur utilisation comme intermediaires de synthese |
| TW510928B (en) * | 2000-09-14 | 2002-11-21 | Toray Du Pont Kk | Manufacture method of heat-resistant shrinkable thread |
| US20080081913A1 (en) * | 2006-09-29 | 2008-04-03 | General Electric Company | Benzoxazole and benzothiazole compounds and methods therefor |
| US20080081210A1 (en) * | 2006-09-29 | 2008-04-03 | General Electric Company | Authenticatable articles and methods therefor |
| WO2014074778A1 (en) | 2012-11-09 | 2014-05-15 | Jacobus Pharmaceutical Company, Inc. | Aryl derivatives and uses thereof |
| US9409893B2 (en) * | 2012-11-09 | 2016-08-09 | Jacobus Pharmaceutical Company, Inc. | Heteroaryl derivatives and uses thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3162642A (en) * | 1960-07-15 | 1964-12-22 | Nat Marking Mach Co | Fluorescent pigments |
| US3491106A (en) * | 1967-12-15 | 1970-01-20 | Gaf Corp | Sodium 3-(2-benzothiazolyl) - 4-hydroxy-benzenesulfonates and analogues thereof |
| US3647812A (en) * | 1969-04-22 | 1972-03-07 | Richard F Smith | Halogenated 2(2'-hydroxyphenyl benzothiazoles |
-
0
- BE BE786758D patent/BE786758A/xx unknown
-
1971
- 1971-07-30 US US00167838A patent/US3723449A/en not_active Expired - Lifetime
-
1972
- 1972-05-23 GB GB2417172A patent/GB1339373A/en not_active Expired
- 1972-06-27 CA CA145,764A patent/CA990300A/en not_active Expired
- 1972-07-26 NL NL7210317A patent/NL7210317A/xx unknown
- 1972-07-28 DE DE2237080A patent/DE2237080A1/de active Pending
- 1972-07-28 FR FR7227222A patent/FR2149129A5/fr not_active Expired
- 1972-07-28 JP JP47075213A patent/JPS4825027A/ja active Pending
-
1978
- 1978-04-20 JP JP4598978A patent/JPS5448760A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3723449A (en) | 1973-03-27 |
| BE786758A (fr) | 1973-01-26 |
| NL7210317A (enExample) | 1973-02-01 |
| GB1339373A (en) | 1973-12-05 |
| CA990300A (en) | 1976-06-01 |
| FR2149129A5 (enExample) | 1973-03-23 |
| JPS5448760A (en) | 1979-04-17 |
| JPS4825027A (enExample) | 1973-04-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |