SK285681B6 - Spôsob chlórmetylácie tiofénu - Google Patents
Spôsob chlórmetylácie tiofénu Download PDFInfo
- Publication number
- SK285681B6 SK285681B6 SK1354-2003A SK13542003A SK285681B6 SK 285681 B6 SK285681 B6 SK 285681B6 SK 13542003 A SK13542003 A SK 13542003A SK 285681 B6 SK285681 B6 SK 285681B6
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- chloromethylation
- thiophene
- compound
- process according
- Prior art date
Links
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims description 52
- 229930192474 thiophene Natural products 0.000 title claims description 26
- 238000007265 chloromethylation reaction Methods 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 31
- 125000000468 ketone group Chemical group 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
- FUOHKPSBGLXIRL-UHFFFAOYSA-N 2-(chloromethyl)thiophene Chemical compound ClCC1=CC=CS1 FUOHKPSBGLXIRL-UHFFFAOYSA-N 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 11
- 229930194542 Keto Natural products 0.000 claims description 10
- 239000007789 gas Substances 0.000 claims description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 8
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 6
- 229920002866 paraformaldehyde Polymers 0.000 claims description 6
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 3
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- CLSHQIDDCJTHAJ-UHFFFAOYSA-N 2-thienylacetonitrile Chemical compound N#CCC1=CC=CS1 CLSHQIDDCJTHAJ-UHFFFAOYSA-N 0.000 abstract description 7
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000013543 active substance Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 7
- 239000008186 active pharmaceutical agent Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- KKWWFYAKOFXBEY-UHFFFAOYSA-N 3-(chloromethyl)thiophene Chemical compound ClCC=1C=CSC=1 KKWWFYAKOFXBEY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- -1 keto compound Chemical class 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- OJBWNBCXVFAMEX-UHFFFAOYSA-N 2,5-bis(chloromethyl)thiophene Chemical compound ClCC1=CC=C(CCl)S1 OJBWNBCXVFAMEX-UHFFFAOYSA-N 0.000 description 2
- JZSRHKOFXIACDX-UHFFFAOYSA-N 2-(thiophen-2-ylmethyl)thiophene Chemical compound C=1C=CSC=1CC1=CC=CS1 JZSRHKOFXIACDX-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- GWZCLMWEJWPFFA-UHFFFAOYSA-N 2-thiophen-3-ylacetonitrile Chemical compound N#CCC=1C=CSC=1 GWZCLMWEJWPFFA-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXRPNLIUCUKLPK-UHFFFAOYSA-N 2-(1-thiophen-2-ylethyl)thiophene Chemical compound C=1C=CSC=1C(C)C1=CC=CS1 CXRPNLIUCUKLPK-UHFFFAOYSA-N 0.000 description 1
- JOIVULVUCVIERM-UHFFFAOYSA-N 2-(2-chloro-1-thiophen-2-ylethyl)thiophene Chemical compound C=1C=CSC=1C(CCl)C1=CC=CS1 JOIVULVUCVIERM-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 description 1
- RZUXCXVPQXRSCO-UHFFFAOYSA-N 3-methyl-2-(2-methylpropyl)thiophene Chemical compound CC(C)CC=1SC=CC=1C RZUXCXVPQXRSCO-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- XQDXMILGABOCEO-UHFFFAOYSA-N ClCC1=CSC(=C1)CO Chemical compound ClCC1=CSC(=C1)CO XQDXMILGABOCEO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002602 strong irritant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- ZPHGMBGIFODUMF-UHFFFAOYSA-N thiophen-2-ylmethanol Chemical compound OCC1=CC=CS1 ZPHGMBGIFODUMF-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Control Of Charge By Means Of Generators (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0102118A HU0102118D0 (en) | 2001-05-22 | 2001-05-22 | Process for chloromethylation |
| PCT/HU2002/000042 WO2002094806A1 (en) | 2001-05-22 | 2002-05-16 | Chloromethylation of thiophene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK13542003A3 SK13542003A3 (sk) | 2004-07-07 |
| SK285681B6 true SK285681B6 (sk) | 2007-06-07 |
Family
ID=89979350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1354-2003A SK285681B6 (sk) | 2001-05-22 | 2002-05-16 | Spôsob chlórmetylácie tiofénu |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7462725B2 (cs) |
| EP (1) | EP1392672B1 (cs) |
| JP (1) | JP4467890B2 (cs) |
| KR (1) | KR100859386B1 (cs) |
| CN (1) | CN1260224C (cs) |
| AT (1) | ATE294790T1 (cs) |
| BR (1) | BRPI0209874B1 (cs) |
| CA (1) | CA2447440C (cs) |
| CZ (1) | CZ301166B6 (cs) |
| DE (1) | DE60204014T2 (cs) |
| DK (1) | DK1392672T3 (cs) |
| ES (1) | ES2240738T3 (cs) |
| HR (1) | HRP20031068B1 (cs) |
| HU (1) | HU0102118D0 (cs) |
| MX (1) | MXPA03010594A (cs) |
| PL (1) | PL210713B1 (cs) |
| PT (1) | PT1392672E (cs) |
| SI (1) | SI1392672T1 (cs) |
| SK (1) | SK285681B6 (cs) |
| WO (1) | WO2002094806A1 (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104513225A (zh) * | 2013-10-08 | 2015-04-15 | 华东师范大学 | 2-噻吩乙腈的制备方法 |
| CN103880741A (zh) * | 2014-02-28 | 2014-06-25 | 安徽国星生物化学有限公司 | 一种2-氯甲基-3，5-二甲基-4-烷氧基吡啶-n-氧化物的制备方法 |
| CN103992302A (zh) * | 2014-06-16 | 2014-08-20 | 商丘凯瑞达化工有限公司 | 2-噻吩乙酸合成工艺 |
| CN104327040A (zh) * | 2014-10-11 | 2015-02-04 | 华东师范大学 | 一种2-噻吩乙酸的合成方法 |
| WO2017139491A1 (en) * | 2016-02-10 | 2017-08-17 | Primus Green Energy Inc. | Single-loop octane enrichment |
| CN113896709B (zh) * | 2021-11-22 | 2023-02-28 | 南京一苇医药科技有限公司 | 一种苯并噻吩-3-乙酸的合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2527680A (en) * | 1945-06-21 | 1950-10-31 | Monsanto Chemicals | Alpha thenyl chloride from hydrogen chloride-formaldehyde solution and thiophene |
| GB639438A (en) * | 1948-02-25 | 1950-06-28 | Ici Ltd | Preparation of organic nitriles |
| US4501903A (en) * | 1983-07-05 | 1985-02-26 | Stauffer Chemical Company | Chloromethylation process |
| FR2608607B1 (fr) * | 1986-12-23 | 1989-04-28 | Sanofi Sa | Procede de preparation de thienylethylamines et dithienylethylamines ainsi obtenues |
| PL158225B1 (en) * | 1989-06-09 | 1992-08-31 | Method for manufacturing 2-chlormethylthiopen |
-
2001
- 2001-05-22 HU HU0102118A patent/HU0102118D0/hu unknown
-
2002
- 2002-05-16 DE DE60204014T patent/DE60204014T2/de not_active Expired - Lifetime
- 2002-05-16 AT AT02727810T patent/ATE294790T1/de active
- 2002-05-16 SI SI200230143T patent/SI1392672T1/xx unknown
- 2002-05-16 MX MXPA03010594A patent/MXPA03010594A/es active IP Right Grant
- 2002-05-16 KR KR1020037015114A patent/KR100859386B1/ko active IP Right Grant
- 2002-05-16 DK DK02727810T patent/DK1392672T3/da active
- 2002-05-16 CZ CZ20032973A patent/CZ301166B6/cs not_active IP Right Cessation
- 2002-05-16 US US10/478,238 patent/US7462725B2/en active Active
- 2002-05-16 JP JP2002591479A patent/JP4467890B2/ja not_active Expired - Fee Related
- 2002-05-16 CN CNB028103882A patent/CN1260224C/zh not_active Expired - Lifetime
- 2002-05-16 BR BRPI0209874A patent/BRPI0209874B1/pt not_active IP Right Cessation
- 2002-05-16 PT PT02727810T patent/PT1392672E/pt unknown
- 2002-05-16 SK SK1354-2003A patent/SK285681B6/sk not_active IP Right Cessation
- 2002-05-16 ES ES02727810T patent/ES2240738T3/es not_active Expired - Lifetime
- 2002-05-16 PL PL363923A patent/PL210713B1/pl unknown
- 2002-05-16 EP EP02727810A patent/EP1392672B1/en not_active Expired - Lifetime
- 2002-05-16 CA CA2447440A patent/CA2447440C/en not_active Expired - Lifetime
- 2002-05-16 WO PCT/HU2002/000042 patent/WO2002094806A1/en active IP Right Grant
-
2003
- 2003-12-19 HR HR20031068A patent/HRP20031068B1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60204014D1 (de) | 2005-06-09 |
| HRP20031068B1 (en) | 2011-12-31 |
| ES2240738T3 (es) | 2005-10-16 |
| CN1260224C (zh) | 2006-06-21 |
| CZ20032973A3 (en) | 2004-03-17 |
| SK13542003A3 (sk) | 2004-07-07 |
| DE60204014T2 (de) | 2006-02-02 |
| JP2004532247A (ja) | 2004-10-21 |
| WO2002094806A1 (en) | 2002-11-28 |
| US7462725B2 (en) | 2008-12-09 |
| KR100859386B1 (ko) | 2008-09-22 |
| CZ301166B6 (cs) | 2009-11-25 |
| CA2447440A1 (en) | 2002-11-28 |
| US20060161008A1 (en) | 2006-07-20 |
| PL363923A1 (en) | 2004-11-29 |
| KR20040018373A (ko) | 2004-03-03 |
| MXPA03010594A (es) | 2004-04-02 |
| HU0102118D0 (en) | 2001-07-30 |
| PL210713B1 (pl) | 2012-02-29 |
| ATE294790T1 (de) | 2005-05-15 |
| PT1392672E (pt) | 2005-08-31 |
| CN1511148A (zh) | 2004-07-07 |
| EP1392672B1 (en) | 2005-05-04 |
| HRP20031068A2 (en) | 2004-04-30 |
| BR0209874A (pt) | 2004-06-08 |
| EP1392672A1 (en) | 2004-03-03 |
| DK1392672T3 (da) | 2005-08-29 |
| JP4467890B2 (ja) | 2010-05-26 |
| SI1392672T1 (en) | 2005-10-31 |
| BRPI0209874B1 (pt) | 2016-03-22 |
| CA2447440C (en) | 2010-10-19 |
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