CN1858042A - 2-丁基-3-(4-羟基-3,5-二碘苯甲酰)苯骈呋喃的合成工艺 - Google Patents
2-丁基-3-(4-羟基-3,5-二碘苯甲酰)苯骈呋喃的合成工艺 Download PDFInfo
- Publication number
- CN1858042A CN1858042A CN 200610051888 CN200610051888A CN1858042A CN 1858042 A CN1858042 A CN 1858042A CN 200610051888 CN200610051888 CN 200610051888 CN 200610051888 A CN200610051888 A CN 200610051888A CN 1858042 A CN1858042 A CN 1858042A
- Authority
- CN
- China
- Prior art keywords
- benzofuran
- butyl
- diiodo
- mol ratio
- hydroxyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- UPHDLVSDDCIKQE-UHFFFAOYSA-N (2-butyl-1-benzofuran-3-yl)-(2-hydroxy-3,5-diiodophenyl)methanone Chemical compound CCCCC1=C(C(=O)C2=C(O)C(I)=CC(I)=C2)C2=CC=CC=C2O1 UPHDLVSDDCIKQE-UHFFFAOYSA-N 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- 239000002253 acid Substances 0.000 claims abstract description 19
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 18
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 18
- OVJKFJDEVKABNF-UHFFFAOYSA-N 2-butyl-1-benzofuran Chemical compound C1=CC=C2OC(CCCC)=CC2=C1 OVJKFJDEVKABNF-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011230 binding agent Substances 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 14
- ZHGKQUXXASLVQQ-UHFFFAOYSA-N (2-Butylbenzofuran-3-yl)(4-hydroxyphenyl)ketone Chemical compound CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 ZHGKQUXXASLVQQ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011630 iodine Substances 0.000 claims abstract description 9
- PNFMEGSMKIHDFZ-UHFFFAOYSA-N (2-Butylbenzofuran-3-yl)(4-hydroxy-3,5-diiodophenyl)ketone Chemical compound CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(O)C(I)=C1 PNFMEGSMKIHDFZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 claims abstract description 8
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000758 substrate Substances 0.000 claims abstract description 4
- 230000001335 demethylating effect Effects 0.000 claims abstract description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 15
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 12
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 6
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical group [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 claims description 5
- BYHPOMNOQNFPBI-UHFFFAOYSA-N 1-benzofuran-2-yl-(4-hydroxy-3,5-diiodophenyl)methanone Chemical compound C1=C(I)C(O)=C(I)C=C1C(=O)C1=CC2=CC=CC=C2O1 BYHPOMNOQNFPBI-UHFFFAOYSA-N 0.000 claims description 4
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 4
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
- YGLPDRIMFIXNBI-UHFFFAOYSA-N methyl 2-bromohexanoate Chemical group CCCCC(Br)C(=O)OC YGLPDRIMFIXNBI-UHFFFAOYSA-N 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- KOUAQOCYMAENKN-UHFFFAOYSA-N ethyl 2-bromohexanoate Chemical compound CCCCC(Br)C(=O)OCC KOUAQOCYMAENKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002191 fatty alcohols Chemical class 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 150000002602 lanthanoids Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- -1 sodium alkoxide Chemical class 0.000 claims description 2
- 238000010992 reflux Methods 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003416 antiarrhythmic agent Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 208000005156 Dehydration Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
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CNB2006100518887A CN100457745C (zh) | 2006-06-09 | 2006-06-09 | 2-丁基-3-(4-羟基-3,5-二碘苯甲酰)苯并呋喃的合成工艺 |
Applications Claiming Priority (1)
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CNB2006100518887A CN100457745C (zh) | 2006-06-09 | 2006-06-09 | 2-丁基-3-(4-羟基-3,5-二碘苯甲酰)苯并呋喃的合成工艺 |
Publications (2)
Publication Number | Publication Date |
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CN1858042A true CN1858042A (zh) | 2006-11-08 |
CN100457745C CN100457745C (zh) | 2009-02-04 |
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CNB2006100518887A Expired - Fee Related CN100457745C (zh) | 2006-06-09 | 2006-06-09 | 2-丁基-3-(4-羟基-3,5-二碘苯甲酰)苯并呋喃的合成工艺 |
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CN (1) | CN100457745C (zh) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102653529A (zh) * | 2011-10-25 | 2012-09-05 | 广东医学院 | 一种苯并呋喃的制备工艺 |
CN104262304A (zh) * | 2014-09-12 | 2015-01-07 | 杨俊� | 一种盐酸胺碘酮的合成方法 |
WO2018039843A1 (zh) * | 2016-08-29 | 2018-03-08 | 沈建美 | 草甘膦的制备工艺 |
CN108440470A (zh) * | 2018-04-20 | 2018-08-24 | 瑞孚信江苏药业股份有限公司 | 一种2-丁基-3-(4-羟基苯甲酰基)苯并呋喃的合成方法 |
CN108675972A (zh) * | 2018-08-01 | 2018-10-19 | 北京嘉林药业股份有限公司 | 一种盐酸胺碘酮中间体2-丁基苯并呋喃的制备方法 |
CN109988131A (zh) * | 2017-12-29 | 2019-07-09 | 浙江普利药业有限公司 | 盐酸胺碘酮的制备方法 |
IT202100031259A1 (it) | 2021-12-14 | 2023-06-14 | Cambrex Profarmaco Milano S R L | Processo per la preparazione di benzofurani |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5364880A (en) * | 1993-06-16 | 1994-11-15 | Advanced Therapies, Inc. | Compound for treatment of cardiac arrhythmia, synthesis, and methods of use |
US6372783B1 (en) * | 1999-10-15 | 2002-04-16 | Aryx Therapeutics | Enantiomeric compounds for treatment of cardiac arrhythmias and methods of use |
-
2006
- 2006-06-09 CN CNB2006100518887A patent/CN100457745C/zh not_active Expired - Fee Related
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102653529A (zh) * | 2011-10-25 | 2012-09-05 | 广东医学院 | 一种苯并呋喃的制备工艺 |
CN104262304A (zh) * | 2014-09-12 | 2015-01-07 | 杨俊� | 一种盐酸胺碘酮的合成方法 |
WO2018039843A1 (zh) * | 2016-08-29 | 2018-03-08 | 沈建美 | 草甘膦的制备工艺 |
CN109988131A (zh) * | 2017-12-29 | 2019-07-09 | 浙江普利药业有限公司 | 盐酸胺碘酮的制备方法 |
CN108440470A (zh) * | 2018-04-20 | 2018-08-24 | 瑞孚信江苏药业股份有限公司 | 一种2-丁基-3-(4-羟基苯甲酰基)苯并呋喃的合成方法 |
CN108675972A (zh) * | 2018-08-01 | 2018-10-19 | 北京嘉林药业股份有限公司 | 一种盐酸胺碘酮中间体2-丁基苯并呋喃的制备方法 |
CN108675972B (zh) * | 2018-08-01 | 2020-09-11 | 北京嘉林药业股份有限公司 | 一种盐酸胺碘酮中间体2-丁基苯并呋喃的制备方法 |
IT202100031259A1 (it) | 2021-12-14 | 2023-06-14 | Cambrex Profarmaco Milano S R L | Processo per la preparazione di benzofurani |
WO2023110528A1 (en) | 2021-12-14 | 2023-06-22 | Cambrex Profarmaco Milano S.R.L. | Process for the preparation of benzofurans |
Also Published As
Publication number | Publication date |
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CN100457745C (zh) | 2009-02-04 |
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