DE1159453B - Verfahren zur Herstellung von Derivaten von 3-Alkyl-3'-methyl-spiro-[benzthiazolin-2,2'-(2'H-1'-benzopyran)] - Google Patents
Verfahren zur Herstellung von Derivaten von 3-Alkyl-3'-methyl-spiro-[benzthiazolin-2,2'-(2'H-1'-benzopyran)]Info
- Publication number
- DE1159453B DE1159453B DEN18614A DEN0018614A DE1159453B DE 1159453 B DE1159453 B DE 1159453B DE N18614 A DEN18614 A DE N18614A DE N0018614 A DEN0018614 A DE N0018614A DE 1159453 B DE1159453 B DE 1159453B
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- group
- ethyl
- radicals
- alkyl
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- -1 AUyI Chemical group 0.000 claims description 4
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- QECVIPBZOPUTRD-UHFFFAOYSA-N N=S(=O)=O Chemical group N=S(=O)=O QECVIPBZOPUTRD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 1
- PEDOSWZBWWCOAY-UHFFFAOYSA-N 2-aminobenzenethiol;hydron;chloride Chemical compound Cl.NC1=CC=CC=C1S PEDOSWZBWWCOAY-UHFFFAOYSA-N 0.000 description 1
- CVULGJIRGZVJHQ-UHFFFAOYSA-N 2-ethylbenzothiazole Chemical compound C1=CC=C2SC(CC)=NC2=C1 CVULGJIRGZVJHQ-UHFFFAOYSA-N 0.000 description 1
- IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RHEXVFGJNGKXIA-UHFFFAOYSA-M CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC=C2[N+](C)=C(CC)SC2=C1 Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC=C2[N+](C)=C(CC)SC2=C1 RHEXVFGJNGKXIA-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82771959A | 1959-07-17 | 1959-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1159453B true DE1159453B (de) | 1963-12-19 |
Family
ID=25249971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEN18614A Pending DE1159453B (de) | 1959-07-17 | 1960-07-12 | Verfahren zur Herstellung von Derivaten von 3-Alkyl-3'-methyl-spiro-[benzthiazolin-2,2'-(2'H-1'-benzopyran)] |
Country Status (6)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514320A (en) * | 1980-10-27 | 1985-04-30 | Petrolite Corporation | Halide free corrosion inhibitors |
| US4525296A (en) * | 1980-10-27 | 1985-06-25 | Petrolite Corporation | Halide free corrosion inhibitors |
| US4539140A (en) * | 1980-10-27 | 1985-09-03 | Petrolite Corporation | Mixtures of non-halogen salts of nitrogen heterocyclics and nitrogen-sulfur heterocyclics |
| US4559163A (en) * | 1980-10-27 | 1985-12-17 | Petrolite Corporation | Halide free octahydrophenanthridine corrosion inhibitors |
-
0
- NL NL253900D patent/NL253900A/xx unknown
- NL NL123748D patent/NL123748C/xx active
-
1960
- 1960-07-01 GB GB23084/60A patent/GB887902A/en not_active Expired
- 1960-07-12 DE DEN18614A patent/DE1159453B/de active Pending
- 1960-07-13 CH CH799260A patent/CH395095A/fr unknown
- 1960-07-13 FR FR832861A patent/FR1262398A/fr not_active Expired
- 1960-07-15 SE SE6928/60A patent/SE305874B/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514320A (en) * | 1980-10-27 | 1985-04-30 | Petrolite Corporation | Halide free corrosion inhibitors |
| US4525296A (en) * | 1980-10-27 | 1985-06-25 | Petrolite Corporation | Halide free corrosion inhibitors |
| US4539140A (en) * | 1980-10-27 | 1985-09-03 | Petrolite Corporation | Mixtures of non-halogen salts of nitrogen heterocyclics and nitrogen-sulfur heterocyclics |
| US4559163A (en) * | 1980-10-27 | 1985-12-17 | Petrolite Corporation | Halide free octahydrophenanthridine corrosion inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| SE305874B (US07816562-20101019-C00012.png) | 1968-11-11 |
| NL123748C (US07816562-20101019-C00012.png) | |
| CH395095A (fr) | 1965-07-15 |
| FR1262398A (fr) | 1961-05-26 |
| NL253900A (US07816562-20101019-C00012.png) | |
| GB887902A (en) | 1962-01-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH633038A5 (de) | Lichtschutzmittel. | |
| DE69126284T2 (de) | Photochrome Indolinospirobenzoxazine und Verfahren zu ihrer Herstellung | |
| DE2025816B2 (de) | Waermeempfindliche kopierblaetter | |
| DE963296C (de) | Verfahren und Material zur Herstellung von photographischen Farbbildern | |
| DE2842263C2 (US07816562-20101019-C00012.png) | ||
| DE1294382B (de) | Substituierte Spiro-[(2'H-1'-benzopyran)-2, 2'-indoline] | |
| DE1178704B (de) | Diazotypiematerial | |
| DE1159453B (de) | Verfahren zur Herstellung von Derivaten von 3-Alkyl-3'-methyl-spiro-[benzthiazolin-2,2'-(2'H-1'-benzopyran)] | |
| DE1522385A1 (de) | Lichtempfindliche Materialien | |
| DE1471677C3 (de) | Warmeentwickelbares Kopierblatt | |
| DE1266763B (de) | Verfahren zur Herstellung von in 3-Stellung substituierten Indol- und Indazolderivaten | |
| DE1002625B (de) | Gegen Einwirkung der Ultraviolettstrahlung geschuetztes photographisches Material | |
| Davidson | Murexide and leucomurexide | |
| DE1204232B (de) | Verfahren zur Herstellung von Derivaten von 3-Alkyl-3'-methyl-spiro[benzoxazolin-2, 2'-(2'H-1'-benzopyran)] | |
| DE1694412A1 (de) | Verfahren zum Faerben von synthetischen linearen Polyestern in der Masse | |
| DE1206879B (de) | Verfahren zur Herstellung von p-Aminoarylaldehyden | |
| DE1178843B (de) | Verfahren zur Herstellung von Abkoemmlingen des 2, 3-Dimethoxy-5-methyl-1, 4-benzohydro-chinons und -chinons | |
| DE2841322C2 (US07816562-20101019-C00012.png) | ||
| DE1668990A1 (de) | Halogensubstituierte p-(p-Alkoxyphenoxy)-phenoxyalkancarbonsaeuren und die entsprechenden Alkylester und Alkancarbonsaeureamide | |
| DE2262127B2 (de) | 6-(N-Alkyl-N-arylamino)-fluorane und deren Verwendung als Farbbildner in druck- und wärmeempfindlichen Kopiermaterialien | |
| DE2454695C2 (de) | Naphthofurane, Verfahren zu deren Herstellung und deren Verwendung | |
| DE1192665B (de) | Waermeempfindliche Kopierschichten | |
| DE2232364C3 (de) | Spirodipyrane | |
| DE1900857A1 (de) | Lichtempfindliche Diazoniumverbindungen fuer das Diazotypie-Photoreproduktionsverfahren | |
| DE595188C (de) | Verfahren zur Darstellung von 4-Aminodiphenylaminderivaten |
