AT390060B - Verfahren zur herstellung von 5-chlor-3chlorsulfonyl-2-thiophencarbonsaeureestern - Google Patents
Verfahren zur herstellung von 5-chlor-3chlorsulfonyl-2-thiophencarbonsaeureestern Download PDFInfo
- Publication number
- AT390060B AT390060B AT0112388A AT112388A AT390060B AT 390060 B AT390060 B AT 390060B AT 0112388 A AT0112388 A AT 0112388A AT 112388 A AT112388 A AT 112388A AT 390060 B AT390060 B AT 390060B
- Authority
- AT
- Austria
- Prior art keywords
- chlorine gas
- compound
- iron
- solvent
- mole
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000002148 esters Chemical class 0.000 title description 2
- 239000002253 acid Substances 0.000 title 1
- KBPATLFUIJOBGP-UHFFFAOYSA-N 5-chloro-3-chlorosulfonylthiophene-2-carboxylic acid Chemical class OC(=O)C=1SC(Cl)=CC=1S(Cl)(=O)=O KBPATLFUIJOBGP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002505 iron Chemical class 0.000 claims abstract description 3
- 238000005660 chlorination reaction Methods 0.000 claims abstract 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 39
- 229910052742 iron Inorganic materials 0.000 claims description 19
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000004913 activation Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 239000011877 solvent mixture Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 3
- 239000005457 ice water Substances 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 238000004817 gas chromatography Methods 0.000 claims 2
- 239000012074 organic phase Substances 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000009826 distribution Methods 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 238000011081 inoculation Methods 0.000 claims 1
- PJVJBDAUWILEOG-UHFFFAOYSA-N methyl 3-chlorosulfonylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1S(Cl)(=O)=O PJVJBDAUWILEOG-UHFFFAOYSA-N 0.000 claims 1
- 239000012071 phase Substances 0.000 claims 1
- 238000005191 phase separation Methods 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- -1 2-pyridyl-carbamoyl Chemical group 0.000 description 2
- CQSJDKGNONPQOQ-UHFFFAOYSA-N 3-aminothiophene-2-carboxylic acid Chemical compound NC=1C=CSC=1C(O)=O CQSJDKGNONPQOQ-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003356 anti-rheumatic effect Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 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
- C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (35)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0112388A AT390060B (de) | 1988-05-02 | 1988-05-02 | Verfahren zur herstellung von 5-chlor-3chlorsulfonyl-2-thiophencarbonsaeureestern |
| AT89106153T ATE92056T1 (de) | 1988-05-02 | 1989-04-07 | Verfahren zur herstellung von 5-chlor-3chlorsulfonyl-2-thiophencarbonsaeureestern. |
| CA000596140A CA1333177C (en) | 1988-05-02 | 1989-04-07 | Process for the preparation of 5-chloro-3-chloro- sulphonyl-2-thiophenecarboxylic acid esters |
| EP89106153A EP0340472B1 (de) | 1988-05-02 | 1989-04-07 | Verfahren zur Herstellung von 5-Chlor-3-chlorsulfonyl-2-thiophencarbonsäureestern |
| ES89106153T ES2058372T3 (es) | 1988-05-02 | 1989-04-07 | Procedimiento para la obtencion de esteres del acido 5-cloro-3-clorosulfonil-2-tiofenocarboxilico. |
| DE8989106153T DE58905010D1 (de) | 1988-05-02 | 1989-04-07 | Verfahren zur herstellung von 5-chlor-3-chlorsulfonyl-2-thiophencarbonsaeureestern. |
| IL89902A IL89902A0 (en) | 1988-05-02 | 1989-04-10 | Preparation of 5-chloro-3-chlorosulphonyl-2 thiophene-carboxylic acid esters |
| MYPI89000456A MY103874A (en) | 1988-05-02 | 1989-04-11 | Process for the preparation of 5-chloro-3-chlorosulpho- nyl-2-thiophenecarboxylic acid esters. |
| NZ228772A NZ228772A (en) | 1988-05-02 | 1989-04-17 | Process for the preparation of 5-chloro-3-chlorosulphonyl-2-thiophene carboxylic acid esters |
| ZA892791A ZA892791B (en) | 1988-05-02 | 1989-04-17 | Process for the preparation of 5-chloro-3-chlorosulphonyl-2-thiophenecarboxylic acid esters |
| SI8910810A SI8910810A (sl) | 1988-05-02 | 1989-04-19 | Postopek za pripravo estrov 5-klor-3-klorsulfonil-2-tiofenkarboksilne kisline |
| YU81089A YU48507B (sh) | 1988-05-02 | 1989-04-19 | Postupak za dobijanje estara 5-hlor-3-hlorsulfonil-2-tiofenkarboksilne kiseline |
| NO891679A NO171912C (no) | 1988-05-02 | 1989-04-24 | Fremgangsmaate for fremstilling av 5-klor-3-klorsulfonyl-2-tiofenkarboksylsyreestere |
| SU894613917A SU1704632A3 (ru) | 1988-05-02 | 1989-04-25 | Способ получени сложных эфиров 5-хлор-3-хлорсульфонил-2-тиофенкарбоновой кислоты |
| EG21189A EG20136A (en) | 1988-05-02 | 1989-04-26 | Process for the preparation of 5-chloro-3-chloro-2-thiophenecarloxylic acid esters |
| PH38579A PH27581A (en) | 1988-05-02 | 1989-04-27 | Process for the preparation of 5-chloro-3-chlorosulphonyl-2-thiophenecarboxylic acid esters |
| AU33801/89A AU614058B2 (en) | 1988-05-02 | 1989-04-27 | Process for the preparation of 5-chloro-3-chlorosulphonyl-2- thiophenecarboxylic acid esters |
| HU892021A HU202518B (en) | 1988-05-02 | 1989-04-27 | Process for producing 5-chloro-3-chloro-sulfonyl-2-thiophenecarboxylic acid esters |
| DD89328037A DD283818A5 (de) | 1988-05-02 | 1989-04-27 | Verfahren zur herstellung von 5-chlor-3-chlorsulfonyl-2-thiophencarbonsaeureestern |
| FI892051A FI86062C (fi) | 1988-05-02 | 1989-04-28 | Foerfarande foer framstaellning av 5-klor-3-klorsulfonyl-2-tiofenkarboksylsyraestrar. |
| CS892634A CS275851B6 (en) | 1988-05-02 | 1989-04-28 | Process for preparing 5-chloro-3-chlorosulfonyl-2-thiophenecarboxylic acid esters |
| CN89102950A CN1028101C (zh) | 1988-05-02 | 1989-04-29 | 5-氯-3-氯磺酰基-2-噻吩羧酸酯的制备方法 |
| KR1019890005804A KR970000685B1 (ko) | 1988-05-02 | 1989-05-01 | 5-클로로-3-클로로설포닐-2-티오펜카복실산 에스테르의 제조방법 |
| DK198902111A DK172655B1 (da) | 1988-05-02 | 1989-05-01 | Fremgangsmåde til fremstilling af 5-chlor-3-chlorsulfonyl-2-thiophencarboxylsyreestere ved chlorering under tilstedeværelse |
| JP1109261A JP2785132B2 (ja) | 1988-05-02 | 1989-05-01 | ５‐クロル‐３‐クロルスルホニル‐２‐チオフエンカルボン酸エステルの製造方法 |
| SA89100027A SA89100027B1 (ar) | 1988-05-02 | 1989-10-07 | عملية لتحضير استرات-( 5-كلورو-3- كلورسولفونيل -2-تيوفين حمض كربوكسيل ) |
| US07/800,702 US5138072A (en) | 1988-05-02 | 1991-12-02 | Process for the preparation of 5-chloro-3-chlorosulphonyl-2-thiophenecarboxylic acid esters |
| GR930400602T GR3008623T3 (en, 2012) | 1988-05-02 | 1993-07-29 | |
| LTRP1204A LT2533B (lt) | 1988-05-02 | 1993-09-28 | 5-chlor-3-chlorsulfonil-2-tiofenkarbonine s rugsties esteriu gavimo budas |
| SG117993A SG117993G (en) | 1988-05-02 | 1993-10-26 | Process for the preparatio of 5-chloro 3-chlorosulphonyl- 2-thiophene-carboxylic esters. |
| LV931216A LV5702A3 (lv) | 1988-05-02 | 1993-11-12 | 5-Hlor-3-hlorsulfonil-2-tiofenkarbonskabes esteru iegusanas panemiens |
| HK1281/93A HK128193A (en) | 1988-05-02 | 1993-11-18 | Process for the preparation of 5-chloro-3-chlorosulphonyl-2-thiophene-carboxylic esters |
| MD94-0070A MD57C2 (ro) | 1988-05-02 | 1994-03-25 | Procedeu de obţinere a eterilor compuşi ai acidului 5-clor-3-clorsulfonil-2-tiofencarbonic |
| CY175694A CY1756A (en) | 1988-05-02 | 1994-06-03 | Process for the preparation of 5-chloro-3-chlorosulphonylthiophene 2-carboxylic acid esters |
| HRP-810/89A HRP940828B1 (en) | 1988-05-02 | 1994-10-26 | Process for the preparation of 5-chloro-3-chlorosulphonyl-2-thiopene-carboxylic esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0112388A AT390060B (de) | 1988-05-02 | 1988-05-02 | Verfahren zur herstellung von 5-chlor-3chlorsulfonyl-2-thiophencarbonsaeureestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA112388A ATA112388A (de) | 1989-08-15 |
| AT390060B true AT390060B (de) | 1990-03-12 |
Family
ID=3507085
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0112388A AT390060B (de) | 1988-05-02 | 1988-05-02 | Verfahren zur herstellung von 5-chlor-3chlorsulfonyl-2-thiophencarbonsaeureestern |
| AT89106153T ATE92056T1 (de) | 1988-05-02 | 1989-04-07 | Verfahren zur herstellung von 5-chlor-3chlorsulfonyl-2-thiophencarbonsaeureestern. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT89106153T ATE92056T1 (de) | 1988-05-02 | 1989-04-07 | Verfahren zur herstellung von 5-chlor-3chlorsulfonyl-2-thiophencarbonsaeureestern. |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5138072A (en, 2012) |
| EP (1) | EP0340472B1 (en, 2012) |
| JP (1) | JP2785132B2 (en, 2012) |
| KR (1) | KR970000685B1 (en, 2012) |
| CN (1) | CN1028101C (en, 2012) |
| AT (2) | AT390060B (en, 2012) |
| AU (1) | AU614058B2 (en, 2012) |
| CA (1) | CA1333177C (en, 2012) |
| CS (1) | CS275851B6 (en, 2012) |
| CY (1) | CY1756A (en, 2012) |
| DD (1) | DD283818A5 (en, 2012) |
| DE (1) | DE58905010D1 (en, 2012) |
| DK (1) | DK172655B1 (en, 2012) |
| EG (1) | EG20136A (en, 2012) |
| ES (1) | ES2058372T3 (en, 2012) |
| FI (1) | FI86062C (en, 2012) |
| GR (1) | GR3008623T3 (en, 2012) |
| HK (1) | HK128193A (en, 2012) |
| HU (1) | HU202518B (en, 2012) |
| IL (1) | IL89902A0 (en, 2012) |
| MY (1) | MY103874A (en, 2012) |
| NO (1) | NO171912C (en, 2012) |
| NZ (1) | NZ228772A (en, 2012) |
| PH (1) | PH27581A (en, 2012) |
| SA (1) | SA89100027B1 (en, 2012) |
| SU (1) | SU1704632A3 (en, 2012) |
| YU (1) | YU48507B (en, 2012) |
| ZA (1) | ZA892791B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4232417A1 (de) * | 1992-09-28 | 1994-03-31 | Bayer Ag | Substituierte Thienylsulfonylharnstoffe |
| DE19540737A1 (de) * | 1995-11-02 | 1997-05-07 | Bayer Ag | Substituierte Sulfonylamino(thio)carbonylverbindungen |
| JP2008514547A (ja) | 2004-05-23 | 2008-05-08 | ハウシー・ファーマシューティカルズ・インコーポレーテッド | セラミューテイン・モジュレーター |
| US8431110B2 (en) * | 2005-05-23 | 2013-04-30 | Hmi Medical Innovations, Llc. | Compounds and method of identifying, synthesizing, optimizing and profiling protein modulators |
| EP4424838A3 (en) * | 2005-11-23 | 2024-12-04 | Gerard M. Housey | Compounds and methods of identifying, synthesizing, optimizing and profiling protein modulators |
| RU2359968C2 (ru) * | 2007-01-17 | 2009-06-27 | Институт нефтехимии и катализа РАН | Способ получения метиловых эфиров 2-тиофенкарбоновой кислоты и ее производных |
| CN116693498B (zh) * | 2023-05-30 | 2024-01-30 | 湖北广济医药科技有限公司 | 一种利用连续流动反应合成5-氯-3-(氯磺酰基)-2-噻吩羧酸甲酯的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2159156A (en) * | 1984-05-24 | 1985-11-27 | Du Pont | Process for the preparation of alkyl 3-chlorosulfonylthiophene-2-carboxylate |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE698778C (de) * | 1934-11-11 | 1941-07-10 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung von organischen Monochlor- oder Monobromverbindungen |
| DE2227439B2 (de) * | 1972-06-06 | 1977-05-05 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Chlorierung oder bromierung phenolischer verbindungen |
| DE2534689B2 (de) * | 1974-09-16 | 1979-03-01 | Basf Ag, 6700 Ludwigshafen | 23-Dihydro-3-oxo-thieno-isothiazol-1,1-dioxide |
| AU518216B2 (en) * | 1977-09-06 | 1981-09-17 | Hafslund Nycomed Pharma Aktiengesellschaft | Thienothiazine derivatives |
| FI862513A7 (fi) * | 1985-07-04 | 1987-01-05 | Chemie Linz Ag | Uudet tieno-1,2-tiatsolijohdokset, menetelmä niiden valmistamiseksi ja näitä sisältävät farmaseuttiset tuotteet. |
| DE3785694T2 (de) * | 1986-05-13 | 1993-09-16 | Seitetsu Kagaku Co Ltd | Thiophenderivate und verfahren zu ihrer herstellung. |
-
1988
- 1988-05-02 AT AT0112388A patent/AT390060B/de not_active IP Right Cessation
-
1989
- 1989-04-07 CA CA000596140A patent/CA1333177C/en not_active Expired - Lifetime
- 1989-04-07 DE DE8989106153T patent/DE58905010D1/de not_active Expired - Lifetime
- 1989-04-07 EP EP89106153A patent/EP0340472B1/de not_active Expired - Lifetime
- 1989-04-07 ES ES89106153T patent/ES2058372T3/es not_active Expired - Lifetime
- 1989-04-07 AT AT89106153T patent/ATE92056T1/de not_active IP Right Cessation
- 1989-04-10 IL IL89902A patent/IL89902A0/xx unknown
- 1989-04-11 MY MYPI89000456A patent/MY103874A/en unknown
- 1989-04-17 NZ NZ228772A patent/NZ228772A/xx unknown
- 1989-04-17 ZA ZA892791A patent/ZA892791B/xx unknown
- 1989-04-19 YU YU81089A patent/YU48507B/sh unknown
- 1989-04-24 NO NO891679A patent/NO171912C/no not_active IP Right Cessation
- 1989-04-25 SU SU894613917A patent/SU1704632A3/ru active
- 1989-04-26 EG EG21189A patent/EG20136A/xx active
- 1989-04-27 PH PH38579A patent/PH27581A/en unknown
- 1989-04-27 AU AU33801/89A patent/AU614058B2/en not_active Expired
- 1989-04-27 DD DD89328037A patent/DD283818A5/de not_active IP Right Cessation
- 1989-04-27 HU HU892021A patent/HU202518B/hu unknown
- 1989-04-28 FI FI892051A patent/FI86062C/fi not_active IP Right Cessation
- 1989-04-28 CS CS892634A patent/CS275851B6/cs not_active IP Right Cessation
- 1989-04-29 CN CN89102950A patent/CN1028101C/zh not_active Expired - Lifetime
- 1989-05-01 DK DK198902111A patent/DK172655B1/da not_active IP Right Cessation
- 1989-05-01 KR KR1019890005804A patent/KR970000685B1/ko not_active Expired - Lifetime
- 1989-05-01 JP JP1109261A patent/JP2785132B2/ja not_active Expired - Lifetime
- 1989-10-07 SA SA89100027A patent/SA89100027B1/ar unknown
-
1991
- 1991-12-02 US US07/800,702 patent/US5138072A/en not_active Expired - Lifetime
-
1993
- 1993-07-29 GR GR930400602T patent/GR3008623T3/el unknown
- 1993-11-18 HK HK1281/93A patent/HK128193A/xx not_active IP Right Cessation
-
1994
- 1994-06-03 CY CY175694A patent/CY1756A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2159156A (en) * | 1984-05-24 | 1985-11-27 | Du Pont | Process for the preparation of alkyl 3-chlorosulfonylthiophene-2-carboxylate |
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