HUP9902375A2 - Eljárás 2-metoxi-4(N-t-butilamino-karbonil)-benzolszulfoklorid előállítására - Google Patents
Eljárás 2-metoxi-4(N-t-butilamino-karbonil)-benzolszulfoklorid előállításáraInfo
- Publication number
- HUP9902375A2 HUP9902375A2 HU9902375A HUP9902375A HUP9902375A2 HU P9902375 A2 HUP9902375 A2 HU P9902375A2 HU 9902375 A HU9902375 A HU 9902375A HU P9902375 A HUP9902375 A HU P9902375A HU P9902375 A2 HUP9902375 A2 HU P9902375A2
- Authority
- HU
- Hungary
- Prior art keywords
- acid
- formula
- methoxy
- resulting
- chloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- DNUYOWCKBJFOGS-UHFFFAOYSA-N 2-[[10-(2,2-dicarboxyethyl)anthracen-9-yl]methyl]propanedioic acid Chemical compound C1=CC=C2C(CC(C(=O)O)C(O)=O)=C(C=CC=C3)C3=C(CC(C(O)=O)C(O)=O)C2=C1 DNUYOWCKBJFOGS-UHFFFAOYSA-N 0.000 abstract 2
- RFXNLHJLTSWQDE-UHFFFAOYSA-N 3-hydroxy-4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C(O)=C1 RFXNLHJLTSWQDE-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N meta--hydroxybenzoic acid Natural products OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 238000006277 sulfonation reaction Methods 0.000 abstract 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 abstract 2
- VQCHPXGONTUEPJ-UHFFFAOYSA-N 3-methoxy-4-sulfobenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1S(O)(=O)=O VQCHPXGONTUEPJ-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 239000003444 phase transfer catalyst Substances 0.000 abstract 1
- 239000002516 radical scavenger Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000542 sulfonic acid group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/57—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
- C07C309/60—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A találmány tárgya eljárás (I) képletű 2-metoxi-4-(N-t-butilamino-karbonil)-benzolszulfoklorid előállítására m-hidroxi-benzoesav szulfonálásával, a kapottszulfonsav vagy sója hidroxi-csoportjának metilezésével, a karboxil- és szulfonsavcsoportsavkloriddá való alakításával és a 4-klórszulfonil-3-metoxi-benzoilklorid t-butilaminnal való reagáltatásával, azzal jellemezve,hogy az m-hidroxi-benzoesav szulfonálását 96 t%-os kénsavban hajtjákvégre, a kapott 3-hidroxi-4-szulfo-benzoesavat (IV) általános képletűsója - mely képletben Z jelentése alkálifém vagy ammóniumcsoport -formájában elkülönítik, majd fázistranszfer-katalizátor jelenlétében11,5 fölötti pH értéken metilezik, a kapott 3-metoxi-4-szulfo-benzoesav-monosót (VI) képletű savkloriddá alakítják, majd savmegkötőszer jelenlétében alacsony hőmérsékleten, poláris oldószeres közegbenmoláris vagy kis feleslegben alkalmazott t-butilaminnal reagáltatják. Ó
Priority Applications (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU9902375A HU225150B1 (en) | 1999-07-15 | 1999-07-15 | Novel process for producing 2-methoxy-4-(t-butylaminocarbonyl)-benzenesulfonyl chloride |
AT00949824T ATE261430T1 (de) | 1999-07-15 | 2000-07-13 | Verfahren zur herstellung von 2-methoxy-4-(n-t- butylamino-carbonyl)-benzolsulfonsaürechlorid |
SK47-2002A SK286031B6 (sk) | 1999-07-15 | 2000-07-13 | Spôsob prípravy 2-metoxy-4-(N-terc- butylaminokarbonyl)benzénsulfonylchloridu |
CNB008102945A CN1164571C (zh) | 1999-07-15 | 2000-07-13 | 制备2-甲氧基-4-(n-叔丁基氨基羰基)苯磺酰氯的方法 |
PL352466A PL199425B1 (pl) | 1999-07-15 | 2000-07-13 | Nowy sposób wytwarzania chlorku 2-metoksy-4-(N-t-butyloaminokarbonylo)-benzenosulfonylu |
PCT/HU2000/000080 WO2001005754A1 (en) | 1999-07-15 | 2000-07-13 | Method for the preparation of 2-methoxy-4-(n-t-butylamino-carbonyl)-benzenesulfonyl chloride |
CA002378337A CA2378337C (en) | 1999-07-15 | 2000-07-13 | Method for the preparation of 2-methoxy-4-(n-t-butylamino-carbonyl)-benzenesulfonyl chloride |
JP2001511415A JP4636761B2 (ja) | 1999-07-15 | 2000-07-13 | 2−メトキシ−4−(N−t−ブチルアミノカルボニル)ベンゼンスルホニルクロリドの製造方法 |
ES00949824T ES2215699T3 (es) | 1999-07-15 | 2000-07-13 | Proceso para la preparacion de cloruro de 2-metoxi-4-(n-t-butilaminocarbonil)bencenosulfonilo. |
CZ2002146A CZ2002146A3 (cs) | 1999-07-15 | 2000-07-13 | Způsob přípravy 2-methoxy-4-(N-terc-butylaminokarbonyl)-benzensulfonylchloridu |
EP00949824A EP1202960B1 (en) | 1999-07-15 | 2000-07-13 | Method for the preparation of 2-methoxy-4-(n-t-butylamino-carbonyl)-benzenesulfonyl chloride |
HU0201573A HU225237B1 (en) | 1999-07-15 | 2000-07-13 | Method for the preparation of 2-methoxy-4-(t-butylamino-carbonyl)-benzenesulfonyl chloride |
MXPA01013342A MXPA01013342A (es) | 1999-07-15 | 2000-07-13 | Metodo para la preparacion de cloruro de 2-metoxi-4-(n-t-butilamino-carbonil)-bencensulfonilo. |
SI200030355T SI1202960T1 (en) | 1999-07-15 | 2000-07-13 | Method for the preparation of 2-methoxy-4-(n-t-butylamino-carbonyl)-benzenesulfonyl chloride |
US10/030,655 US6548702B1 (en) | 1999-07-15 | 2000-07-13 | Method for the preparation of 2-methoxy-4-(N-t-butylamino-carbonyl)-benzenesulfonyl chloride |
DE60008884T DE60008884T2 (de) | 1999-07-15 | 2000-07-13 | Verfahren zur herstellung von 2-methoxy-4-(n-t-butylamino-carbonyl)-benzolsulfonsaürechlorid |
AU63083/00A AU6308300A (en) | 1999-07-15 | 2000-07-13 | Method for the preparation of 2-methoxy-4-(n-t-butylamino-carbonyl)-benzenesulfonyl chloride |
BRPI0012430-3A BR0012430B1 (pt) | 1999-07-15 | 2000-07-13 | método para a preparação de cloreto de 2-metóxi-4-(n-t-butilamino-carbonil)-benzenosulfoni la. |
HR20020141A HRP20020141B1 (en) | 1999-07-15 | 2002-02-14 | METHOD FOR THE PREPARATION OF 2-METHOXY-4-(N-t-BUTYLAMINO-CARBONYL)-BENZENESULFONYL CHLORIDE |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU9902375A HU225150B1 (en) | 1999-07-15 | 1999-07-15 | Novel process for producing 2-methoxy-4-(t-butylaminocarbonyl)-benzenesulfonyl chloride |
Publications (4)
Publication Number | Publication Date |
---|---|
HU9902375D0 HU9902375D0 (en) | 1999-10-28 |
HUP9902375A2 true HUP9902375A2 (hu) | 2001-05-28 |
HUP9902375A3 HUP9902375A3 (en) | 2002-11-28 |
HU225150B1 HU225150B1 (en) | 2006-07-28 |
Family
ID=89998737
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU9902375A HU225150B1 (en) | 1999-07-15 | 1999-07-15 | Novel process for producing 2-methoxy-4-(t-butylaminocarbonyl)-benzenesulfonyl chloride |
Country Status (17)
Country | Link |
---|---|
US (1) | US6548702B1 (hu) |
EP (1) | EP1202960B1 (hu) |
JP (1) | JP4636761B2 (hu) |
CN (1) | CN1164571C (hu) |
AT (1) | ATE261430T1 (hu) |
AU (1) | AU6308300A (hu) |
BR (1) | BR0012430B1 (hu) |
CA (1) | CA2378337C (hu) |
CZ (1) | CZ2002146A3 (hu) |
DE (1) | DE60008884T2 (hu) |
ES (1) | ES2215699T3 (hu) |
HR (1) | HRP20020141B1 (hu) |
HU (1) | HU225150B1 (hu) |
MX (1) | MXPA01013342A (hu) |
PL (1) | PL199425B1 (hu) |
SK (1) | SK286031B6 (hu) |
WO (1) | WO2001005754A1 (hu) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MXPA04000949A (es) * | 2001-07-31 | 2004-06-25 | Sanofi Synthelabo | Proceso para la preparacion de derivados de 3-espiroæciclohexam-1,3æ-æ3h!indolin-2æ-ona!. |
CN105621518A (zh) * | 2015-12-29 | 2016-06-01 | 浙江奇彩环境科技股份有限公司 | 一种3,4-二氯苯磺酸废水的资源化处理方法 |
CN110372548A (zh) * | 2018-04-12 | 2019-10-25 | 南京化学试剂股份有限公司 | 一种5-磺基水杨酸的精制方法 |
CN113402437B (zh) * | 2021-06-29 | 2023-07-14 | 河北维达康生物科技有限公司 | 一种合成膳食补充剂褪黑素的新方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3953507A (en) | 1973-08-31 | 1976-04-27 | Stauffer Chemical Company | N-t-butyl-α-(3,5-substituted phenoxy) alkyl amides and their use as herbicides |
FR2740136B1 (fr) * | 1995-10-24 | 1998-01-09 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et les compositions pharmaceutiques les contenant |
FR2757157B1 (fr) * | 1996-12-13 | 1999-12-31 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant |
-
1999
- 1999-07-15 HU HU9902375A patent/HU225150B1/hu not_active IP Right Cessation
-
2000
- 2000-07-13 BR BRPI0012430-3A patent/BR0012430B1/pt not_active IP Right Cessation
- 2000-07-13 CN CNB008102945A patent/CN1164571C/zh not_active Expired - Fee Related
- 2000-07-13 AU AU63083/00A patent/AU6308300A/en not_active Abandoned
- 2000-07-13 CA CA002378337A patent/CA2378337C/en not_active Expired - Fee Related
- 2000-07-13 EP EP00949824A patent/EP1202960B1/en not_active Expired - Lifetime
- 2000-07-13 JP JP2001511415A patent/JP4636761B2/ja not_active Expired - Fee Related
- 2000-07-13 ES ES00949824T patent/ES2215699T3/es not_active Expired - Lifetime
- 2000-07-13 DE DE60008884T patent/DE60008884T2/de not_active Expired - Lifetime
- 2000-07-13 US US10/030,655 patent/US6548702B1/en not_active Expired - Fee Related
- 2000-07-13 CZ CZ2002146A patent/CZ2002146A3/cs unknown
- 2000-07-13 MX MXPA01013342A patent/MXPA01013342A/es active IP Right Grant
- 2000-07-13 AT AT00949824T patent/ATE261430T1/de not_active IP Right Cessation
- 2000-07-13 SK SK47-2002A patent/SK286031B6/sk not_active IP Right Cessation
- 2000-07-13 WO PCT/HU2000/000080 patent/WO2001005754A1/en active IP Right Grant
- 2000-07-13 PL PL352466A patent/PL199425B1/pl not_active IP Right Cessation
-
2002
- 2002-02-14 HR HR20020141A patent/HRP20020141B1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
BR0012430B1 (pt) | 2011-05-17 |
SK472002A3 (en) | 2003-02-04 |
HUP9902375A3 (en) | 2002-11-28 |
WO2001005754A1 (en) | 2001-01-25 |
CN1360569A (zh) | 2002-07-24 |
AU6308300A (en) | 2001-02-05 |
JP2003505366A (ja) | 2003-02-12 |
BR0012430A (pt) | 2002-03-26 |
EP1202960B1 (en) | 2004-03-10 |
ATE261430T1 (de) | 2004-03-15 |
CN1164571C (zh) | 2004-09-01 |
HU225150B1 (en) | 2006-07-28 |
JP4636761B2 (ja) | 2011-02-23 |
HU9902375D0 (en) | 1999-10-28 |
CZ2002146A3 (cs) | 2002-11-13 |
PL199425B1 (pl) | 2008-09-30 |
DE60008884T2 (de) | 2005-02-03 |
HRP20020141A2 (en) | 2003-10-31 |
US6548702B1 (en) | 2003-04-15 |
MXPA01013342A (es) | 2002-08-20 |
EP1202960A1 (en) | 2002-05-08 |
PL352466A1 (en) | 2003-08-25 |
DE60008884D1 (de) | 2004-04-15 |
HRP20020141B1 (en) | 2010-09-30 |
ES2215699T3 (es) | 2004-10-16 |
CA2378337C (en) | 2008-05-20 |
CA2378337A1 (en) | 2001-01-25 |
SK286031B6 (sk) | 2008-01-07 |
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Legal Events
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MM4A | Lapse of definitive patent protection due to non-payment of fees |