SE423388B - Forfarande for framstellning av halogensulfonyltiofenkarbonsyraforeningar - Google Patents

Forfarande for framstellning av halogensulfonyltiofenkarbonsyraforeningar

Info

Publication number: SE423388B
Authority: SE; Sweden
Prior art keywords: acid; parts; compound; formula; reaction
Prior art date: 1977-01-05

Application number

SE7714971A

Other languages

English (en)

Swedish (sv)

Other versions

SE7714971L (sv

Inventor

P A Rossy

W Hoffmann

N Mueller

Original Assignee

Basf Ag

Priority date (The priority date 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 date listed.)

1977-01-05

Filing date

1977-12-30

Publication date

1982-05-03

1977-01-05 Priority claimed from DE2700261A external-priority patent/DE2700261C2/de

1977-04-20 Priority claimed from DE19772717477 external-priority patent/DE2717477C2/de

1977-12-30 Application filed by Basf Ag filed Critical Basf Ag

1978-07-06 Publication of SE7714971L publication Critical patent/SE7714971L/xx

1982-05-03 Publication of SE423388B publication Critical patent/SE423388B/sv

Links

239000002253 acid Substances 0.000 title claims description 21
150000001875 compounds Chemical class 0.000 title claims description 21
238000000034 method Methods 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
229920001021 polysulfide Polymers 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
239000005077 polysulfide Substances 0.000 claims abstract description 5
150000008117 polysulfides Polymers 0.000 claims abstract description 5
-1 3-ketothiophenecarboxylic acid compound Chemical class 0.000 claims description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
108090000623 proteins and genes Proteins 0.000 claims 1
238000006243 chemical reaction Methods 0.000 abstract description 30
239000007858 starting material Substances 0.000 abstract description 20
231100000252 nontoxic Toxicity 0.000 abstract description 7
230000003000 nontoxic effect Effects 0.000 abstract description 7
239000007795 chemical reaction product Substances 0.000 abstract description 6
230000015572 biosynthetic process Effects 0.000 abstract description 5
235000003599 food sweetener Nutrition 0.000 abstract description 5
239000003765 sweetening agent Substances 0.000 abstract description 5
150000003460 sulfonic acids Chemical class 0.000 abstract description 4
238000003786 synthesis reaction Methods 0.000 abstract description 4
206010013911 Dysgeusia Diseases 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
238000004519 manufacturing process Methods 0.000 abstract description 3
229910052783 alkali metal Inorganic materials 0.000 abstract description 2
150000001340 alkali metals Chemical class 0.000 abstract description 2
230000000202 analgesic effect Effects 0.000 abstract description 2
230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
230000003356 anti-rheumatic effect Effects 0.000 abstract description 2
206010012601 diabetes mellitus Diseases 0.000 abstract description 2
229940079593 drug Drugs 0.000 abstract description 2
239000000975 dye Substances 0.000 abstract description 2
239000000047 product Substances 0.000 abstract description 2
CAVNWXJINLMELC-UHFFFAOYSA-N 1,1-dioxo-1,2-benzothiazol-3-one thiophene Chemical class C=1C=CSC=1.C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CAVNWXJINLMELC-UHFFFAOYSA-N 0.000 abstract 1
239000004129 EU approved improving agent Substances 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 abstract 1
239000011814 protection agent Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 19
239000002904 solvent Substances 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000126 substance Substances 0.000 description 10
150000003839 salts Chemical class 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
239000012024 dehydrating agents‎ Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000012467 final product Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000000243 solution Substances 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
235000013305 food Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
235000019204 saccharin Nutrition 0.000 description 3
SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 2
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical class OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 description 2
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical class OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 description 2
IQOJIHIRSVQTJJ-UHFFFAOYSA-N 3-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(Cl)=C1 IQOJIHIRSVQTJJ-UHFFFAOYSA-N 0.000 description 2
VWWFEZXWHBORHN-UHFFFAOYSA-N 3-chlorosulfonylthiophene-2-carboxylic acid Chemical class OC(=O)C=1SC=CC=1S(Cl)(=O)=O VWWFEZXWHBORHN-UHFFFAOYSA-N 0.000 description 2
ZCLXQTGLKVQKFD-UHFFFAOYSA-N 3-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1 ZCLXQTGLKVQKFD-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
PGBFYLVIMDQYMS-UHFFFAOYSA-N Methyl thiophene-2-carboxylate Chemical compound COC(=O)C1=CC=CS1 PGBFYLVIMDQYMS-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
235000009508 confectionery Nutrition 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000000605 extraction Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
MRFIBCNQYJJOPN-UHFFFAOYSA-N methyl 4-chlorosulfonylthiophene-3-carboxylate Chemical compound COC(=O)C1=CSC=C1S(Cl)(=O)=O MRFIBCNQYJJOPN-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
231100000956 nontoxicity Toxicity 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
238000005406 washing Methods 0.000 description 2
PDVFSPNIEOYOQL-UHFFFAOYSA-N (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(C)C=C1 PDVFSPNIEOYOQL-UHFFFAOYSA-N 0.000 description 1
QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 1
GKNWQHIXXANPTN-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)F GKNWQHIXXANPTN-UHFFFAOYSA-N 0.000 description 1
XBWQFDNGNOOMDZ-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoropropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F XBWQFDNGNOOMDZ-UHFFFAOYSA-N 0.000 description 1
ACEKLXZRZOWKRY-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,5-undecafluoropentane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ACEKLXZRZOWKRY-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 description 1
RCGMVCCNAAVDBT-UHFFFAOYSA-N 1,1-dioxothieno[3,4-d][1,2]thiazol-3-one Chemical compound S1C=C2C(=O)NS(=O)(=O)C2=C1 RCGMVCCNAAVDBT-UHFFFAOYSA-N 0.000 description 1
GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
XXACHQRFXDSJNO-UHFFFAOYSA-N 1,2-dihydroacenaphthylene-5-sulfonic acid Chemical compound C1CC2=CC=CC3=C2C1=CC=C3S(=O)(=O)O XXACHQRFXDSJNO-UHFFFAOYSA-N 0.000 description 1
DLBPTOMGZXBZOX-UHFFFAOYSA-N 1,2-thiazole 1,1-dioxide Chemical compound O=S1(=O)C=CC=N1 DLBPTOMGZXBZOX-UHFFFAOYSA-N 0.000 description 1
JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
AMCBMCWLCDERHY-UHFFFAOYSA-N 1,3-dichloronaphthalene Chemical compound C1=CC=CC2=CC(Cl)=CC(Cl)=C21 AMCBMCWLCDERHY-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
NQAWQSVOOHTLEY-UHFFFAOYSA-N 1-chlorobutane-1-sulfonic acid Chemical compound CCCC(Cl)S(O)(=O)=O NQAWQSVOOHTLEY-UHFFFAOYSA-N 0.000 description 1
SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
NVJUHMXYKCUMQA-UHFFFAOYSA-N 1-ethoxypropane Chemical compound CCCOCC NVJUHMXYKCUMQA-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
XTDQDBVBDLYELW-UHFFFAOYSA-N 2,2,3-trimethylpentane Chemical compound CCC(C)C(C)(C)C XTDQDBVBDLYELW-UHFFFAOYSA-N 0.000 description 1
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125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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238000011403 purification operation Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
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NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
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HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
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ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

SE7714971A 1977-01-05 1977-12-30 Forfarande for framstellning av halogensulfonyltiofenkarbonsyraforeningar SE423388B (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2700261A DE2700261C2 (de)	1977-01-05	1977-01-05	Verfahren zur Herstellung von 3-Halogensulfonylthiophen-4-carbonsäureverbindungen
DE19772717477 DE2717477C2 (de)	1977-04-20	1977-04-20	Verfahren zur Herstellung von 3-Halogensulfonylthiophen-2-carbonsäureverbindungen

Publications (2)

Publication Number	Publication Date
SE7714971L SE7714971L (sv)	1978-07-06
SE423388B true SE423388B (sv)	1982-05-03

Family

ID=25771425

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7714971A SE423388B (sv)	1977-01-05	1977-12-30	Forfarande for framstellning av halogensulfonyltiofenkarbonsyraforeningar

Country Status (11)

Country	Link
US (1)	US4143050A (da)
JP (1)	JPS6034554B2 (da)
AU (1)	AU512465B2 (da)
CA (1)	CA1097358A (da)
CH (1)	CH631980A5 (da)
DK (1)	DK3078A (da)
ES (1)	ES465761A1 (da)
FR (1)	FR2376857A1 (da)
GB (1)	GB1591071A (da)
NL (1)	NL7800070A (da)
SE (1)	SE423388B (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2015027111A1 (en)	2013-08-21	2015-02-26	Verrica Pharmaceuticals, Inc.	Compositions, methods and systems for the treatment of cutaneous disorders
US11147790B2 (en)	2017-06-06	2021-10-19	Verrica Pharmaceuticals Inc.	Treatment of cutaneous disorders
CA3253199A1 (en)	2017-06-15	2025-10-30	Verrica Pharmaceuticals Inc.	Devices and methods for the treatment of body surface disorders
AU2018346414B2 (en)	2017-10-04	2023-07-06	Verrica Pharmaceuticals, Inc.	Synthesis of cantharidin

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2534689B2 (de) *	1974-09-16	1979-03-01	Basf Ag, 6700 Ludwigshafen	23-Dihydro-3-oxo-thieno-isothiazol-1,1-dioxide

1977
- 1977-12-21 AU AU31835/77A patent/AU512465B2/en not_active Expired
- 1977-12-22 CA CA293,798A patent/CA1097358A/en not_active Expired
- 1977-12-23 US US05/863,913 patent/US4143050A/en not_active Expired - Lifetime
- 1977-12-28 JP JP52157517A patent/JPS6034554B2/ja not_active Expired
- 1977-12-29 FR FR7739589A patent/FR2376857A1/fr active Granted
- 1977-12-30 SE SE7714971A patent/SE423388B/sv unknown
1978
- 1978-01-03 NL NL7800070A patent/NL7800070A/xx not_active Application Discontinuation
- 1978-01-04 DK DK3078A patent/DK3078A/da not_active Application Discontinuation
- 1978-01-04 GB GB123/78A patent/GB1591071A/en not_active Expired
- 1978-01-04 ES ES465761A patent/ES465761A1/es not_active Expired
- 1978-01-05 CH CH12478A patent/CH631980A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
NL7800070A (nl)	1978-07-07
SE7714971L (sv)	1978-07-06
US4143050A (en)	1979-03-06
DK3078A (da)	1978-07-06
FR2376857A1 (fr)	1978-08-04
AU3183577A (en)	1979-06-28
FR2376857B3 (da)	1980-09-26
CA1097358A (en)	1981-03-10
JPS6034554B2 (ja)	1985-08-09
CH631980A5 (de)	1982-09-15
ES465761A1 (es)	1978-09-16
GB1591071A (en)	1981-06-10
JPS5384963A (en)	1978-07-26
AU512465B2 (en)	1980-10-09

Publication	Publication Date	Title
US3041336A (en)	1962-06-26	3-oxo-1.2.6-thiadiazine-1.1-dioxides
US4028373A (en)	1977-06-07	Thiophene saccharines
US4242518A (en)	1980-12-30	Thiophene compounds and their manufacture
US4143050A (en)	1979-03-06	Manufacture of 3-halosulfonylthiophene-carboxylic acid compounds
WO2018210354A1 (zh)	2018-11-22	一种抗痛风药Lesinurad的新型制备方法及其关键中间体
DK155009B (da)	1989-01-23	Analogifremgangsmaade til fremstilling af thienooe2,3-eaa-1,2-thiazin-1,1-dioxidderivat eller farmaceutisk tolerable salte heraf samt udgangsmateriale til brug ved fremgangsmaaden
US3954764A (en)	1976-05-04	Dibenzo [b,f]thiepins bearing piperazinyl substitution
Cope et al.	1956	Syntheses of D-and L-2, 6-diheterobicyclo [3.3. 0] octanes
DE2717477C2 (de)	1985-12-05	Verfahren zur Herstellung von 3-Halogensulfonylthiophen-2-carbonsäureverbindungen
SU1151210A3 (ru)	1985-04-15	Способ получени геминальных дигалоидных производных конденсированных пиримидин-4-онов,рацематов или оптически активных антиподов
DE2700261C2 (de)	1985-07-04	Verfahren zur Herstellung von 3-Halogensulfonylthiophen-4-carbonsäureverbindungen
EP0254577B1 (en)	1989-09-27	Synthesis of bicyclic aromatic sulfonyl chlorides
US3102123A (en)	1963-08-27	Analogues of griseofulvin and process by which they are prepared
DK162392B (da)	1991-10-21	Fremgangsmaade til fremstilling af 1,1-dioxopenicillanoyloxymethyl-6-(2-amino-2-phenylacetamido)penicillanat eller 1,1-dioxopenicillanoyloxymethyl-6-oe2-amino-2-(p-hydroxyphenyl)acetamidoaapenicillanat eller farmaceutisk acceptable syreadditionssalte deraf og dihalogensubstituerede derivater af disse forbindelser til anvendelse som udgangsmateriale ved fremgangsmaaden
SE444810B (sv)	1986-05-12	Sulfinyazetidinonforeningar till anvendning for framstellning av 3-metylencefamsulfoxider
CN102898340A (zh)	2013-01-30	一种s-取代邻氨基苯甲酸硫酯衍生物的合成方法
US3625963A (en)	1971-12-07	Process for the preparation of 3-methanesulphonyl-phenthiazines
CN110498762A (zh)	2019-11-26	一种(2s,5r)-5-[(苄氧基)氨基]-哌啶-2-甲酸乙酯的合成方法
Koster et al.	1978	Chlorination of the cephem dihydrothiazine ring. Factors influencing C-2 substitution vs. degradation to isothiazoles1
NO792632L (no)	1975-08-07	3-cefem-3-sulfonatesterforbindelser for bruk som mellomprodukter ved fremstilling av terapeutisk virksomme forbindelser
US4117004A (en)	1978-09-26	Manufacture of amidosulfonic acids
US3914316A (en)	1975-10-21	Preparation of 2-(sulfur-substituted)-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-ones
CN109897075A (zh)	2019-06-18	一种三氯蔗糖-6-乙酸酯的绿色合成方法
IE861115L (en)	1986-11-21	Thiophenones
US7291742B2 (en)	2007-11-06	Process for the preparation of benzo [d] isoxazol-3-yl-methanesulfonic acid and the intermediates thereof