HRP20150899T1 - Postupak za jodiranje fenolnih derivata - Google Patents
Postupak za jodiranje fenolnih derivata Download PDFInfo
- Publication number
- HRP20150899T1 HRP20150899T1 HRP20150899TT HRP20150899T HRP20150899T1 HR P20150899 T1 HRP20150899 T1 HR P20150899T1 HR P20150899T T HRP20150899T T HR P20150899TT HR P20150899 T HRP20150899 T HR P20150899T HR P20150899 T1 HRP20150899 T1 HR P20150899T1
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- substrate
- compound
- disubstituted phenol
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 18
- 230000026045 iodination Effects 0.000 title claims 2
- 238000006192 iodination reaction Methods 0.000 title claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims 2
- -1 3,5-disubstituted phenol Chemical class 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 9
- 239000000758 substrate Substances 0.000 claims 8
- QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 claims 6
- 239000007864 aqueous solution Substances 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- 239000012736 aqueous medium Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- VAPDZNUFNKUROY-UHFFFAOYSA-N 2,4,6-triiodophenol Chemical class OC1=C(I)C=C(I)C=C1I VAPDZNUFNKUROY-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000007351 Smiles rearrangement reaction Methods 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 239000012045 crude solution Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical compound OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B39/00—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring
Claims (15)
1. Postupak za pripravu spojeva trijodofenola prema formuli 2
[image]
koji sadrži jodiranje 3,5-disupstituiranog fenola s formulom 1,
[image]
ili njegove soli, u vodenom mediju, s molekulskim jodom u prisutnosti jodne kiseline,
naznačen time da:
R i R' predstavljaju, istu ili međusobno različitu, skupinu s formulom -NHR1 ili -NR2R3, pri čemu svaki R1, R2 i R3 je, međusobno neovisno, ravnolančana ili razgranata C1-C6 alkil skupina koja je proizvoljno supstituirana s jednom ili više skupina odabranih iz skupine koju čine hidroksil (-OH), C1-C5 alkoksi ili hidroksialkoksi skupine.
2. Postupak prema zahtjevu 1 naznačen time da, u spojevima s formulama 1 i 2 R i R' predstavljaju, istu ili međusobno različitu, skupinu s formulom -NHR1 ili -NR2R3 pri čemu svaki R1, R2 i R3 je, međusobno neovisno, ravnolančana ili razgranata C1-C4 alkil skupina proizvoljno supstituirana s jednom do tri hidroksil skupine.
3. Postupak prema zahtjevu 2 naznačen time da, u spojevima s formulama 1 i 2, R i R' predstavljaju istu ili međusobno različitu skupinu odabranu između:
-NHCH3,
-NHCH2-CH(OH)-CH2OH,
-NHCH(CH2OH)2, i
-N(CH3)-CH2-CH(OH)-CH2OH.
4. Postupak prema zahtjevu 1 naznačen time da je molarni odnos između molekulskog joda i supstrata 3,5-disupstituiranog fenola 1 [I2/1] od 1.1 do 1.3, a molarni odnos između jodne kiseline i supstrata 3,5-disupstituiranog fenola 1 je od 0.4 do 0.8.
5. Postupak prema zahtjevu 4 naznačen time da se trijodiranje supstrata 3,5-disupstituiranog fenola 1 s jodom i jodnom kiselinom provodi uz korištenje molarnog odnosa supstrata 3,5-disupstituiranog fenola: jod : jodna kiselina od 1:1.2:0.6.
6. Postupak prema bilo kojem od zahtjeva od 1 do 5 naznačen time da navedeni vodeni mediju medij je voda ili vodena otopina.
7. Postupak prema zahtjevu 6 naznačen time da sadrži: dobivanje vodene otopine supstrata 3,5-disupstituiranog fenola s formulom 1, ili njegove soli, te dodavanje I2 i HIO3 u navedenu vodenu otopinu.
8. Postupak prema zahtjevu 7 naznačen time da navedena vodena otopina supstrata 3,5-disupstituiranog fenola je sirova otopina koja proizlazi iz industrijskog procesa i koja sadrži supstrat 3,5-disupstituiranog fenola kao sol.
9. Postupak prema zahtjevima 7-8 naznačen time da sadrži dodavanje krutog I2 u navedenu vodenu otopinu supstrata 3,5-disupstituiranog fenola zagrijanu na temperaturu u rasponu od 20 do 70°C i zatim dodavanje jodne kiseline.
10. Postupak prema zahtjevu 9 naznačen time da se jodna kiselina dodaje kada reakcijska smjesa ima pH u rasponu od 5 do 6.
11. Postupak prema bilo kojem od zahtjeva od 1-10 naznačen time da je vrijeme reakcije u rasponu od 5 do 9 sati.
12. Postupak za pripravu spojeva s formulom 5
[image]
naznačen time da:
R i R' imaju značenja iskazana u zahtjevu 1, i
R4 i R5 su, isti ili međusobno različiti, vodik ili ravnolančana ili razgranata C1-C6 alkil skupina, proizvoljno supstituirana s jednom ili više hidroksil ili C1-C6 alkoksi skupina, koji sadrži:
a) pripremu spoja trijodofenola s formulom 2 prema postupku iz bilo kojeg zahtjeva 1-11; te navedeni postupak nadalje sadrži:
b) reakciju navedenog spoja formule 2, bilo kao takvog ili koji sadrži fenolnu OH skupinu u obliku soli s alkalnim metalom, sa spojem formule 3
R4HN(C=O)CH(R5)Z 3
pri čemu R4 i R5 su, isti ili međusobno različiti, kako je gore definirano, i Z je atom halogena odabran od klora ili broma, ili izlazna skupina odabrana između metansulfoniloksi, benzensulfoniloksi, nitrobenzensulfoniloksi, toluensulfoniloksi, da se dobije spoj s formulom 4
[image]
pri čemu R, R', R4 i R5 imaju gore navedena značenja; i
c) podvrgavanje navedenog spoja formule 4 Smiles-ovom preuređenju u prisutnosti baze, kako bi se dobio spoj formule 5.
13. Postupak prema zahtjevu 12 naznačen time da oba R i R' su -NH-CH(CH2OH)2 skupina, R4 je vodik i R5 je metil skupina.
14. Postupak prema zahtjevu 12 naznačen time da je za pripravu spoja s formulom 5 pri čemu oba R i R' su -NH-CH2-CH(OH)CH2OH, R4 je metil i R5 je vodik.
15. Postupak prema zahtjevu 14 naznačen time da sadrži korake prikazane u Shemi 3:
[image]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10165485A EP2394984A1 (en) | 2010-06-10 | 2010-06-10 | Process for the iodination of phenolic derivatives |
| PCT/EP2011/059594 WO2011154500A1 (en) | 2010-06-10 | 2011-06-09 | Process for the iodination of phenolic derivatives |
| EP11725069.6A EP2580187B1 (en) | 2010-06-10 | 2011-06-09 | Process for the iodination of phenolic derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20150899T1 true HRP20150899T1 (hr) | 2015-10-09 |
Family
ID=42983748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150899TT HRP20150899T1 (hr) | 2010-06-10 | 2015-08-26 | Postupak za jodiranje fenolnih derivata |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8766003B2 (hr) |
| EP (2) | EP2394984A1 (hr) |
| JP (1) | JP5752790B2 (hr) |
| KR (1) | KR101790539B1 (hr) |
| CN (1) | CN103108860B (hr) |
| AU (1) | AU2011263733B2 (hr) |
| CA (1) | CA2803213C (hr) |
| DK (1) | DK2580187T3 (hr) |
| ES (1) | ES2544815T3 (hr) |
| HR (1) | HRP20150899T1 (hr) |
| HU (1) | HUE027028T2 (hr) |
| IL (1) | IL223633A (hr) |
| PL (1) | PL2580187T3 (hr) |
| PT (1) | PT2580187E (hr) |
| RU (1) | RU2563645C2 (hr) |
| SI (1) | SI2580187T1 (hr) |
| WO (1) | WO2011154500A1 (hr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2657238C2 (ru) | 2013-11-05 | 2018-06-09 | Бракко Имэджинг Спа | Способ получения йопамидола |
| JP6743781B2 (ja) * | 2016-08-08 | 2020-08-19 | 信越化学工業株式会社 | レジスト材料及びパターン形成方法 |
| FR3113904B1 (fr) | 2020-09-08 | 2022-08-12 | Innoverda | Procédé de synthèse du 3,5-diiodo-4-hydroxy benzylalcool |
| WO2023046815A1 (en) | 2021-09-24 | 2023-03-30 | Bracco Imaging Spa | Electrochemical iodination of n,n'-(2,3-dihydroxypropyl)-5-hydroxy-1,3-benzenedicarboxamide |
| CN114349605A (zh) * | 2022-02-15 | 2022-04-15 | 营口兴福化工有限公司 | 对碘苯酚合成方法 |
| WO2023209165A1 (en) | 2022-04-29 | 2023-11-02 | Bracco Imaging Spa | Process for the preparation of 2,4,6-triiodophenol derivatives |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU394355A1 (ru) * | 1971-01-12 | 1973-08-22 | Р. М. Кузнецова, В. Н. Костин, К. С. Шаназаров, Г. И. Шарова, И. Бродский, Ф. А. Куцовска , Л. С. Розенштраух | Изомеров йодфенилуидркановых кислот |
| BE795902A (fr) | 1972-02-25 | 1973-08-23 | Rhone Poulenc Sa | Procede de preparation du diiodo-3,5 hydroxy-4benzonitrile et de l'iodo-3 hydroxy-4 nitro-5benzonitrile |
| US3914294A (en) | 1972-06-01 | 1975-10-21 | Squibb & Sons Inc | 3,5-Disubstituted-2,4,6-triiodobenzoic acids |
| ES8507448A1 (es) | 1983-12-16 | 1985-10-01 | Bislak Sociedad Anonima | Procedimiento para la obtencion del 2,4,6 triyodofenol |
| IT1196363B (it) | 1984-12-10 | 1988-11-16 | Bracco Ind Chimica Spa | Derivati dell'acido 5-alcossi-2,4,6-triiodo- o -tribromo-isoftalico,metodo per la loro preparazione e relativi mezzi di contrasto radiologici |
| FR2581641B1 (fr) | 1985-05-10 | 1988-08-12 | Delalande Sa | Procede de preparation d'acides 6-alkoxy(inferieur)-1-naphtoiques et des esters correspondants et utilisation de ce procede pour la preparation d'acides 6-alkoxy(inferieur)-5-halo-1-naphtoiques et des esters correspondants |
| ATE79368T1 (de) | 1987-05-22 | 1992-08-15 | Bracco Spa | Herstellung von 5-acylamino-2,4,6-trijodo- oder tribromo-benzoesaeure-derivate. |
| US5013865A (en) | 1988-04-06 | 1991-05-07 | Mallinckrodt, Inc. | Process for the preparation of 2,4,6-triiodo-5-amino-N-alkylisophthalamic acid and 2,4,6-triiodo-5-amino-isophthalamide compounds |
| US5075502A (en) | 1989-12-13 | 1991-12-24 | Mallinckrodt, Inc. | Nonionic x-ray contrast agents, compositions and methods |
| FR2673180B1 (fr) | 1991-02-25 | 1994-03-04 | Guerbet Sa | Nouveaux composes non ioniques poly-iodes, procede de preparation, produit de contraste les contenant. |
| JPH07233106A (ja) | 1994-02-23 | 1995-09-05 | Fuji Xerox Co Ltd | モノヨウ素化芳香族化合物の製造方法 |
| US5763650A (en) | 1995-05-23 | 1998-06-09 | Fructamine S.P.A. | Process for the preparation of a halosubstituted aromatic acid |
| DE69601525T2 (de) | 1995-05-23 | 1999-06-24 | Fructamine Spa | Verfahren zur herstellung von dicarbonsäurechlorid |
| DE69609963T2 (de) | 1995-05-24 | 2001-04-12 | Nycomed Imaging As | Verfahren zur iodierung |
| IT1277339B1 (it) * | 1995-07-25 | 1997-11-10 | Bracco Spa | Processo per la produzione di agenti contrastografici iodurati |
| IT1303797B1 (it) | 1998-11-27 | 2001-02-23 | Bracco Spa | Processo per la preparazione di n,n'-bis(2,3-diidrossipropil)-5-((idrossiacetil)metilammino)-2,4,6-triiodo-1,3-benzendicarbossammide. |
| JP4434692B2 (ja) | 2003-11-04 | 2010-03-17 | 三菱瓦斯化学株式会社 | ５−ヨード−２−メチル安息香酸の製造方法 |
| EP1777215B1 (en) | 2004-08-10 | 2010-11-03 | Mitsubishi Gas Chemical Company, Inc. | Method for producing 2-amino-5-iodobenzoic acid |
| JPWO2009028608A1 (ja) | 2007-08-31 | 2010-12-02 | 三菱瓦斯化学株式会社 | オルト位がヨウ素置換されたフェノール誘導体の製造方法 |
| EP2093206A1 (en) | 2008-02-20 | 2009-08-26 | BRACCO IMAGING S.p.A. | Process for the iodination of aromatic compounds |
| EP2243767A1 (en) * | 2009-04-21 | 2010-10-27 | Bracco Imaging S.p.A | Process for the iodination of aromatic compounds |
-
2010
- 2010-06-10 EP EP10165485A patent/EP2394984A1/en not_active Withdrawn
-
2011
- 2011-06-09 SI SI201130579T patent/SI2580187T1/sl unknown
- 2011-06-09 ES ES11725069.6T patent/ES2544815T3/es active Active
- 2011-06-09 KR KR1020137000501A patent/KR101790539B1/ko active IP Right Grant
- 2011-06-09 CN CN201180028401.2A patent/CN103108860B/zh active Active
- 2011-06-09 AU AU2011263733A patent/AU2011263733B2/en active Active
- 2011-06-09 RU RU2013100177/04A patent/RU2563645C2/ru active
- 2011-06-09 JP JP2013513700A patent/JP5752790B2/ja active Active
- 2011-06-09 HU HUE11725069A patent/HUE027028T2/en unknown
- 2011-06-09 CA CA2803213A patent/CA2803213C/en active Active
- 2011-06-09 PT PT117250696T patent/PT2580187E/pt unknown
- 2011-06-09 DK DK11725069.6T patent/DK2580187T3/en active
- 2011-06-09 EP EP11725069.6A patent/EP2580187B1/en active Active
- 2011-06-09 WO PCT/EP2011/059594 patent/WO2011154500A1/en active Application Filing
- 2011-06-09 US US13/702,223 patent/US8766003B2/en active Active
- 2011-06-09 PL PL11725069T patent/PL2580187T3/pl unknown
-
2012
- 2012-12-13 IL IL223633A patent/IL223633A/en active IP Right Grant
-
2015
- 2015-08-26 HR HRP20150899TT patent/HRP20150899T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011154500A1 (en) | 2011-12-15 |
| JP2013528199A (ja) | 2013-07-08 |
| ES2544815T3 (es) | 2015-09-04 |
| EP2394984A1 (en) | 2011-12-14 |
| US8766003B2 (en) | 2014-07-01 |
| SI2580187T1 (sl) | 2015-12-31 |
| CA2803213C (en) | 2017-04-25 |
| CN103108860A (zh) | 2013-05-15 |
| US20130072719A1 (en) | 2013-03-21 |
| IL223633A (en) | 2015-09-24 |
| JP5752790B2 (ja) | 2015-07-22 |
| IL223633A0 (en) | 2013-03-05 |
| EP2580187A1 (en) | 2013-04-17 |
| PL2580187T3 (pl) | 2015-10-30 |
| RU2563645C2 (ru) | 2015-09-20 |
| CA2803213A1 (en) | 2011-12-15 |
| HUE027028T2 (en) | 2016-08-29 |
| AU2011263733B2 (en) | 2015-06-11 |
| CN103108860B (zh) | 2015-06-17 |
| EP2580187B1 (en) | 2015-05-27 |
| KR101790539B1 (ko) | 2017-10-26 |
| PT2580187E (pt) | 2015-09-21 |
| KR20130111517A (ko) | 2013-10-10 |
| DK2580187T3 (en) | 2015-08-24 |
| RU2013100177A (ru) | 2014-07-20 |
| AU2011263733A1 (en) | 2013-01-17 |
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