RU2004120783A - Способ получения 2-(2-нитрофенилазо)фенолов без использования органических растворителей - Google Patents
Способ получения 2-(2-нитрофенилазо)фенолов без использования органических растворителей Download PDFInfo
- Publication number
- RU2004120783A RU2004120783A RU2004120783/04A RU2004120783A RU2004120783A RU 2004120783 A RU2004120783 A RU 2004120783A RU 2004120783/04 A RU2004120783/04 A RU 2004120783/04A RU 2004120783 A RU2004120783 A RU 2004120783A RU 2004120783 A RU2004120783 A RU 2004120783A
- Authority
- RU
- Russia
- Prior art keywords
- carbon atoms
- alkyl
- substituted
- branched
- straight
- Prior art date
Links
- 150000002989 phenols Chemical class 0.000 title claims 3
- 239000003960 organic solvent Substances 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 43
- 125000000217 alkyl group Chemical group 0.000 claims 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000003342 alkenyl group Chemical group 0.000 claims 13
- 238000000034 method Methods 0.000 claims 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 11
- 125000003884 phenylalkyl group Chemical group 0.000 claims 10
- -1 2-nitrophenylazo Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 claims 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical group [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims 2
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 235000010288 sodium nitrite Nutrition 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 claims 1
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical class OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims 1
- 125000005569 butenylene group Chemical group 0.000 claims 1
- 125000005622 butynylene group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004956 cyclohexylene group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000005309 thioalkoxy group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C09B29/12—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group of the benzene series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/006—Special methods of performing the coupling reaction characterised by process features
- C09B41/009—Diazotising and coupling in one step
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33848401P | 2001-12-05 | 2001-12-05 | |
| US60/338,484 | 2001-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2004120783A true RU2004120783A (ru) | 2006-01-10 |
Family
ID=23324996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004120783/04A RU2004120783A (ru) | 2001-12-05 | 2002-11-26 | Способ получения 2-(2-нитрофенилазо)фенолов без использования органических растворителей |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7074906B2 (enExample) |
| EP (1) | EP1451254A1 (enExample) |
| JP (1) | JP2005511705A (enExample) |
| KR (1) | KR20050044696A (enExample) |
| CN (1) | CN100341859C (enExample) |
| AU (1) | AU2002356731A1 (enExample) |
| BR (1) | BR0214673A (enExample) |
| CA (1) | CA2465398A1 (enExample) |
| MX (1) | MXPA04005410A (enExample) |
| RU (1) | RU2004120783A (enExample) |
| WO (1) | WO2003048257A1 (enExample) |
| ZA (1) | ZA200403389B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0225548D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Compounds |
| US8669281B1 (en) | 2013-03-14 | 2014-03-11 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
| PT2970101T (pt) | 2013-03-14 | 2018-10-04 | Alkermes Pharma Ireland Ltd | Pró-fármacos de fumaratos e seu uso no tratamento de várias doenças |
| CN103193724B (zh) * | 2013-04-08 | 2016-01-13 | 南通大学 | 一种紫外线吸收剂2,2’-亚甲基二[6-(2h-苯并三唑-2-基)-4-叔丁基]苯酚的制备方法 |
| CA2940845C (en) | 2014-02-24 | 2019-09-24 | Alkermes Pharma Ireland Limited | Sulfonamide and sulfinamide prodrugs of fumarates and their use in treating various diseases |
| CN103965125A (zh) * | 2014-05-06 | 2014-08-06 | 西安近代化学研究所 | 一种3,3’-二硝基-5,5’-联-1,2,4-三唑的合成方法 |
| CN112679979B (zh) * | 2020-12-29 | 2023-09-01 | 浙江永合新材料科技有限公司 | 一种苯并三唑类紫外线吸收剂中间体偶氮染料的制备方法 |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2362988A (en) | 1940-11-26 | 1944-11-21 | Geigy Ag J R | Mordant triazole dyestuffs and process for making the same |
| US2418416A (en) | 1943-12-30 | 1947-04-01 | Du Pont | Manufacture of azo lakes |
| US2478767A (en) | 1945-10-04 | 1949-08-09 | Du Pont | Manufacture of azo compounds |
| US2478768A (en) | 1945-10-04 | 1949-08-09 | Du Pont | Manufacture of azo lakes |
| US3773751A (en) | 1969-09-08 | 1973-11-20 | American Cyanamid Co | Synthesis of nitroaromatic-azophenols |
| US3793305A (en) | 1970-09-14 | 1974-02-19 | Du Pont | One-step process of preparing azo dyes by simultaneous diazotization |
| US3998804A (en) * | 1972-07-11 | 1976-12-21 | Ciba-Geigy Corporation | Process for coupling of water-insoluble 2,4-disubstituted phenols with diazotized o-nitroanilines |
| CH573400A5 (enExample) * | 1972-07-11 | 1976-03-15 | Ciba Geigy Ag | |
| US3978074A (en) | 1973-11-21 | 1976-08-31 | Uniroyal Inc. | Method of making hydroxyarylbenzotriazoles and their N-oxides |
| DE2503714C3 (de) | 1975-01-30 | 1978-05-03 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von wasserlöslichen Azofarbstoffen |
| DE2516032C2 (de) * | 1975-04-12 | 1984-10-04 | Bayer Ag, 5090 Leverkusen | Verfahren zum Diazotieren aromatischer Amine |
| JPS52113973A (en) | 1976-03-19 | 1977-09-24 | Kawaken Fine Chem Co Ltd | Synthesis of benzotriazole derivatives |
| JPS52113974A (en) | 1976-03-19 | 1977-09-24 | Kawaken Fine Chem Co Ltd | Synthesis of benzotriazole derivatives |
| JPS5398932A (en) * | 1977-02-04 | 1978-08-29 | Hitachi Chem Co Ltd | Preparation of o-nitro-o'-hydroxyazobenzenes and 2-(2'-hydroxyphenyl)- 1,2,3-benzotriazoles |
| US4219480A (en) * | 1977-09-20 | 1980-08-26 | Ciba-Geigy Corporation | Process for the production of 2-aryl-2H-benzotriazoles |
| US4230867A (en) * | 1977-11-25 | 1980-10-28 | Ciba-Geigy Corporation | Process for the production of 2-aryl-2H-benzotriazoles |
| EP0006564B1 (de) * | 1978-06-26 | 1981-12-30 | Ciba-Geigy Ag | 2-(2-Hydroxy-3.5-disubstituiertes-phenyl)-2H-benzotriazol und damit stabilisierte Mischungen |
| EP0034836B1 (de) | 1979-05-16 | 1983-07-13 | Ciba-Geigy Ag | Verfahren zum Herstellen von Nitroazobenzolen |
| US4226763A (en) * | 1978-06-26 | 1980-10-07 | Ciba-Geigy Corporation | 2-[2-Hydroxy-3,5-di-(.alpha.,α-dimethylbenzyl)-phenyl]-2H-benzotriazole and stabilized compositions |
| US4347180A (en) * | 1979-05-16 | 1982-08-31 | Ciba-Geigy Corporation | High caustic coupling process for preparing substituted 2-nitro-2'-hydroxyazobenzenes |
| JPS56133076A (en) | 1980-03-25 | 1981-10-17 | Nissan Motor Co Ltd | Painting method of intermediate coat |
| JPS59170172A (ja) | 1983-03-18 | 1984-09-26 | Shuichi Seino | ２−フエニルベンゾトリアゾ−ル類の製造方法 |
| CH655125A5 (de) | 1983-09-21 | 1986-03-27 | Ciba Geigy Ag | Verfahren zur herstellung von azofarbstoffpraeparaten. |
| JPS61197571A (ja) | 1985-02-27 | 1986-09-01 | Kemipuro Kasei Kk | ２−フエニルベンゾトリアゾ−ル−ｎ−オキシド類の製造法 |
| US4789541A (en) | 1985-10-04 | 1988-12-06 | Davis Michael H | Method and composition for in vivo radiolabeling of red blood cells with 99m Tc |
| DE3683772D1 (de) | 1986-08-22 | 1992-03-12 | Chemipro Kasei Kaisha Ltd | Methode zur herstellung von 2-phenylbenzotriazolen und von 2-phenylbenzotriazol-n-oxiden. |
| JPH0798811B2 (ja) | 1986-09-16 | 1995-10-25 | ケミプロ化成株式会社 | ２−フエニルベンゾトリアゾ−ル−ｎ−オキシド類の製造法 |
| JPH0798812B2 (ja) | 1986-09-16 | 1995-10-25 | ケミプロ化成株式会社 | ２−フエニルベンゾトリアゾ−ル類の製造法 |
| JPH0788595B2 (ja) | 1987-01-27 | 1995-09-27 | ケミプロ化成株式会社 | ２−フエニルベンゾトリアゾ−ル類の製造方法 |
| JPH02202880A (ja) * | 1989-01-31 | 1990-08-10 | Kemipuro Kasei Kk | ２―フェニルベンゾトリアゾール類の製造法 |
| JPH02202879A (ja) | 1989-01-31 | 1990-08-10 | Kemipuro Kasei Kk | ２―フェニルベンゾトリアゾール類の製造法 |
| KR100313583B1 (ko) * | 1993-09-16 | 2002-11-23 | 시바 스페셜티 케미칼스 홀딩 인크. | 2,4-이중치환된 페놀과 2-니트로아닐린의 아조커플링 |
| US5571924A (en) | 1995-07-12 | 1996-11-05 | Ciba-Geigy Corporation | Process for the preparation of benzotriazoles |
| US6166218A (en) * | 1996-11-07 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Benzotriazole UV absorbers having enhanced durability |
| US6566507B2 (en) * | 2000-08-03 | 2003-05-20 | Ciba Specialty Chemicals Corporation | Processes for the preparation of benzotriazole UV absorbers |
-
2002
- 2002-11-26 CA CA002465398A patent/CA2465398A1/en not_active Abandoned
- 2002-11-26 JP JP2003549440A patent/JP2005511705A/ja active Pending
- 2002-11-26 EP EP02804196A patent/EP1451254A1/en not_active Withdrawn
- 2002-11-26 BR BR0214673-8A patent/BR0214673A/pt not_active IP Right Cessation
- 2002-11-26 RU RU2004120783/04A patent/RU2004120783A/ru not_active Application Discontinuation
- 2002-11-26 US US10/497,621 patent/US7074906B2/en not_active Expired - Fee Related
- 2002-11-26 KR KR1020047008604A patent/KR20050044696A/ko not_active Withdrawn
- 2002-11-26 AU AU2002356731A patent/AU2002356731A1/en not_active Abandoned
- 2002-11-26 MX MXPA04005410A patent/MXPA04005410A/es not_active Application Discontinuation
- 2002-11-26 WO PCT/EP2002/013292 patent/WO2003048257A1/en not_active Ceased
- 2002-11-26 CN CNB028242904A patent/CN100341859C/zh not_active Expired - Fee Related
-
2004
- 2004-05-05 ZA ZA200403389A patent/ZA200403389B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050044696A (ko) | 2005-05-12 |
| WO2003048257A1 (en) | 2003-06-12 |
| MXPA04005410A (es) | 2004-10-11 |
| US7074906B2 (en) | 2006-07-11 |
| CA2465398A1 (en) | 2003-06-12 |
| CN1599777A (zh) | 2005-03-23 |
| AU2002356731A1 (en) | 2003-06-17 |
| US20050053562A1 (en) | 2005-03-10 |
| ZA200403389B (en) | 2006-06-28 |
| CN100341859C (zh) | 2007-10-10 |
| BR0214673A (pt) | 2004-10-19 |
| EP1451254A1 (en) | 2004-09-01 |
| JP2005511705A (ja) | 2005-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA94 | Acknowledgement of application withdrawn (non-payment of fees) |
Effective date: 20080520 |