GB1388102A - Phenoxy-benzoxazole compounds and their use - Google Patents
Phenoxy-benzoxazole compounds and their useInfo
- Publication number
- GB1388102A GB1388102A GB734173A GB734173A GB1388102A GB 1388102 A GB1388102 A GB 1388102A GB 734173 A GB734173 A GB 734173A GB 734173 A GB734173 A GB 734173A GB 1388102 A GB1388102 A GB 1388102A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- alkyl
- chlorine
- bromine
- fluorine
- 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
- XSPQHOJEUTZTON-UHFFFAOYSA-N 2-phenoxy-1,3-benzoxazole Chemical class N=1C2=CC=CC=C2OC=1OC1=CC=CC=C1 XSPQHOJEUTZTON-UHFFFAOYSA-N 0.000 title abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- 229910052801 chlorine Inorganic materials 0.000 abstract 12
- 239000000460 chlorine Substances 0.000 abstract 12
- 239000001257 hydrogen Substances 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 8
- 229910052794 bromium Inorganic materials 0.000 abstract 8
- 229910052731 fluorine Inorganic materials 0.000 abstract 7
- 239000011737 fluorine Substances 0.000 abstract 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- -1 tetramethylene, trimethylene Chemical group 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 abstract 1
- 238000005282 brightening Methods 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 125000000565 sulfonamide group Chemical group 0.000 abstract 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 abstract 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- 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
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
- C07F9/65324—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
1388102 Phenoxybenzoxazole derivatives CIBA-GEIGY AG 14 Feb 1973 [17 Feb 1972] 7341/73 Headings C2C and C2P Novel phenoxy-benzoxazole compounds have the general formula wherein R 1 represents hydrogen, chlorine, bromine, alkyl with 1 to 12 carbon atoms, alkoxy with 1 to 4 carbon atoms, optionally methyl substituted cyclopentyl or cyclohexyl, or phenylalkyl with 1 to 4 carbon atoms in the alkyl part and which is optionally substituted in the benzene ring by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, R 2 represents hydrogen, chlorine, bromine, alkyl with 1 to 8 carbon atoms or alkoxy with 1 to 4 carbon atoms, or R 1 and R 2 in the o-position to one another together form a fused benzene ring or a tetramethylene, trimethylene or methylenedioxy radical, R 3 represents hydrogen, chlorine or alkyl with 1 to 4 carbon atoms, R 4 represents hydrogen, chlorine, or alkyl with 1 to 4 carbon atoms, and A represents: (a) a radical of the formula wherein R 1 , R 2 , R 3 and R 4 have the abovementioned meaning, or (b) a radical of the formula wherein X 1 denotes hydrogen, fluorine, chlorine, bromine, alkyl with 1 to 12 carbon atoms, optionally methyl-substituted cyclopentyl or cyclohexyl, phenyl optionally substituted by one or more fluorine, chlorine or bromine atoms or (C 1 -C 4 ) alkyl or alkoxy groups, cyano, carboxyl, carbalkoxy with 2 to 12 carbon atoms, a sulpho group or its salts, a sulphonamide group which is optionally substituted at the nitrogen atom by one or two alkyl radicals with 1 to 4 carbon atoms, a sulphonic acid alkyl ester group 1 to 4 carbon atoms or an alkylsulphonyl radical with 1 to 4 carbon atoms, X 2 denotes hydrogen, fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms, a sulpho group or a salts thereof or X 1 and X 2 in the o-position to one another together form a fused benzene ring or a tetramethylene or trimethylene radical, and X 3 denotes hydrogen, chlorine or alkyl with 1 to 4 carbon atoms; or (c) a radical of the formula wherein X 4 denotes hydrogen, fluorine, chlorine, bromine, alkyl with 1 to 12 carbon atoms, optionally methyl-substituted cyclopentyl or cyclohexyl or phenyl optionally substituted by fluorine, chlorine, bromine, alkyl with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms, X 5 denotes hydrogen, fluorine, chlorine, bromine or alkyl with 1 to 4 carbon atoms or X 4 and X 5 in the o-position to one another together form a fused benzene ring. The novel compounds may be used as optical brightening agents. The compounds of the invention may be prepared via a phosphonate of the formula Example 5 describes the preparation of such a phosphonate by reacting a bromide of the formula with triethyl phosphite.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH229872 | 1972-02-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1388102A true GB1388102A (en) | 1975-03-19 |
Family
ID=4230509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB734173A Expired GB1388102A (en) | 1972-02-17 | 1973-02-14 | Phenoxy-benzoxazole compounds and their use |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4912176A (en) |
| DE (1) | DE2306050A1 (en) |
| FR (1) | FR2172248B1 (en) |
| GB (1) | GB1388102A (en) |
| NL (1) | NL7301734A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4208513A (en) * | 1977-11-10 | 1980-06-17 | Ciba-Geigy Corporation | Benzoxazolyl-phenylstilbenes, processes for producing them, and their use as optical brighteners |
| WO2003045929A1 (en) * | 2001-11-26 | 2003-06-05 | Takeda Chemical Industries, Ltd. | Bicyclic derivative, process for producing the same, and use |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH650784A5 (en) * | 1979-12-06 | 1985-08-15 | Ciba Geigy Ag | METHOD FOR PRODUCING BENZAZOLYL COMPOUNDS. |
| DE10308226A1 (en) * | 2003-02-25 | 2004-09-23 | Degussa Ag | Transparent molding compound for optical applications |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1467750A (en) * | 1965-02-15 | 1967-01-27 | Ciba Geigy | New azole compounds, their preparation process and their use |
| CH558442A (en) * | 1969-06-13 | 1975-01-31 |
-
1973
- 1973-02-07 NL NL7301734A patent/NL7301734A/xx not_active Application Discontinuation
- 1973-02-08 DE DE19732306050 patent/DE2306050A1/en not_active Withdrawn
- 1973-02-14 FR FR7305236A patent/FR2172248B1/fr not_active Expired
- 1973-02-14 GB GB734173A patent/GB1388102A/en not_active Expired
- 1973-02-16 JP JP1846973A patent/JPS4912176A/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4208513A (en) * | 1977-11-10 | 1980-06-17 | Ciba-Geigy Corporation | Benzoxazolyl-phenylstilbenes, processes for producing them, and their use as optical brighteners |
| WO2003045929A1 (en) * | 2001-11-26 | 2003-06-05 | Takeda Chemical Industries, Ltd. | Bicyclic derivative, process for producing the same, and use |
| US7622479B2 (en) | 2001-11-26 | 2009-11-24 | Takeda Pharmaceutical Company Limited | Bicyclic derivative, its production and use |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7301734A (en) | 1973-08-21 |
| FR2172248B1 (en) | 1976-06-11 |
| DE2306050A1 (en) | 1973-08-23 |
| JPS4912176A (en) | 1974-02-02 |
| FR2172248A1 (en) | 1973-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1491087A (en) | Benzyl-phenoxyalkane carboxylic acids and derivatives thereof and their use as herbicides | |
| GB1377250A (en) | 4,4-divinyldiphenyl compounds | |
| GB1298577A (en) | New stilbene derivatives | |
| MX9300256A (en) | DERIVATIVES OF ACETIC ACID AND PROCESS FOR ITS PREPARATION. | |
| US4083859A (en) | 13,14-Dihydro-PGD2 compounds | |
| GB1510381A (en) | Dioxaphosphorinane derivatives as flameproofing agents | |
| GB1416116A (en) | Distyryl-benzene derivatives their manufacture and their use | |
| US4119785A (en) | 3,7-Inter-m-phenylene-4,5,6-trinor-12,13(E)-didehydro-13,14-dihydro-9-deoxy-PGD1 compounds | |
| GB1388102A (en) | Phenoxy-benzoxazole compounds and their use | |
| US4145561A (en) | 2-Decarboxy-2-hydroxymethyl-9-deoxy-9-methylene-16-phenyl-PGF compounds | |
| DK41481A (en) | 2-NITRO-5- (SUBSTITUTED PHENOXY) -BENZOATES OF ALFA-HYDROXYAL CANANATES USED AS HERBICIDES | |
| GB1331670A (en) | Quaternised benzofuranylbenzimadzoles | |
| GB1429039A (en) | Dialkylphosphinyl compounds | |
| ATE69043T1 (en) | IODPROPARGYL ESTER OF HYDROXYPHENYL AND HYDROXYPHENOXYALKANOSIC ACIDS. | |
| DE3460039D1 (en) | N-SULPHENYL-PHENETHYL SULFONAMIDE | |
| ATE52504T1 (en) | AROYL-SUBSTITUTED DIHYDRO-1,4-THIAZINE. | |
| GB1474579A (en) | Brominated carbamic esters and their use as flameproofing agents | |
| US4157448A (en) | ω-Aryl-12,13(e)-didehydro-13,14-dihydro-PGD compounds | |
| US4168384A (en) | ω-Aryl-inter-phenylene-12,13(e)-didehydro-13,14-dihydro-PGD1 compounds | |
| US4365075A (en) | ω-Aryl-PGD compounds | |
| US4174456A (en) | 9-Deoxy-9-methylene-inter-oxa-13,14-didehydro-16-phenyl-17,18,19,20-tetranor-PGF1 compounds | |
| GB1450862A (en) | 6-triazolyl-2-benzofurans and optical brighteners | |
| US4211714A (en) | 2,2-Difluoro-trans-4,5,13,14-tetrahydro-PGI1 compounds | |
| GB1324904A (en) | Dibenzothiophene dioxide derivatives | |
| DK362479A (en) | PROCEDURE FOR MANUFACTURING THIOETHERS |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |