CH371124A - Verfahren zur Herstellung von Benzothiadiazin-1,1-dioxyden - Google Patents

Info

Publication number

CH371124A

CH371124A CH6065958A CH6065958A CH371124A CH 371124 A CH371124 A CH 371124A CH 6065958 A CH6065958 A CH 6065958A CH 6065958 A CH6065958 A CH 6065958A CH 371124 A CH371124 A CH 371124A

Authority

CH

Switzerland

Prior art keywords

benzothiadiazine

disulfamylaniline

dioxide

sulfamyl

chloro

Prior art date

1957-06-17

Links

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• 238000000034 method Methods 0.000 title claims description 11
• 238000002360 preparation method Methods 0.000 title claims description 3
• UOCUSOBVEHOMMB-UHFFFAOYSA-N 2h-1$l^{6},2,3-benzothiadiazine 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)NN=CC2=C1 UOCUSOBVEHOMMB-UHFFFAOYSA-N 0.000 title description 3
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 15
• QLGJNQICDRXXGG-UHFFFAOYSA-N (disulfamoylamino)benzene Chemical compound NS(=O)(=O)N(S(N)(=O)=O)C1=CC=CC=C1 QLGJNQICDRXXGG-UHFFFAOYSA-N 0.000 claims description 8
• IHJCXVZDYSXXFT-UHFFFAOYSA-N chloraminophenamide Chemical compound NC1=CC(Cl)=C(S(N)(=O)=O)C=C1S(N)(=O)=O IHJCXVZDYSXXFT-UHFFFAOYSA-N 0.000 claims description 8
• -1 dimethylforman: id Chemical compound 0.000 claims description 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 7
• 239000001257 hydrogen Substances 0.000 claims description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims description 7
• JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 239000011541 reaction mixture Substances 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
• 239000003054 catalyst Substances 0.000 claims description 3
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 150000007513 acids Chemical class 0.000 claims 1
• HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical compound C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 claims 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 239000000243 solution Substances 0.000 description 9
• 150000001875 compounds Chemical class 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 229910021529 ammonia Inorganic materials 0.000 description 4
• 239000000203 mixture Substances 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
• 235000019270 ammonium chloride Nutrition 0.000 description 3
• 125000004432 carbon atom Chemical group C* 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 230000008018 melting Effects 0.000 description 3
• 238000003918 potentiometric titration Methods 0.000 description 3
• 239000002904 solvent Substances 0.000 description 3
• 239000007858 starting material Substances 0.000 description 3
• UYVDLZFIIVODJV-UHFFFAOYSA-N 6-chloro-3-methyl-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound NS(=O)(=O)C1=C(Cl)C=C2NC(C)=NS(=O)(=O)C2=C1 UYVDLZFIIVODJV-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• 238000004519 manufacturing process Methods 0.000 description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 description 2
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 229920005989 resin Polymers 0.000 description 2
• 239000011347 resin Substances 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 125000001424 substituent group Chemical group 0.000 description 2
• CGVXNZNOSZFBCD-UHFFFAOYSA-N 1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound N1=CNS(=O)(=O)C2=CC(S(=O)(=O)N)=CC=C21 CGVXNZNOSZFBCD-UHFFFAOYSA-N 0.000 description 1
• OBZUMOZIMMQMPW-UHFFFAOYSA-N 3-methyl-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(S(N)(=O)=O)C=C2S(=O)(=O)NC(C)=NC2=C1 OBZUMOZIMMQMPW-UHFFFAOYSA-N 0.000 description 1
• YIZXGHNDQUYDDF-UHFFFAOYSA-N 4-amino-6-chlorobenzene-1,3-disulfonyl chloride Chemical compound NC1=CC(Cl)=C(S(Cl)(=O)=O)C=C1S(Cl)(=O)=O YIZXGHNDQUYDDF-UHFFFAOYSA-N 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• ASJYFEVFADVYBY-UHFFFAOYSA-N CC=1NS(C2=C(N=1)C=C(C(=C2)S(N)(=O)=O)[N+](=O)[O-])(=O)=O Chemical compound CC=1NS(C2=C(N=1)C=C(C(=C2)S(N)(=O)=O)[N+](=O)[O-])(=O)=O ASJYFEVFADVYBY-UHFFFAOYSA-N 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• AJTSGHFOJGUPKV-UHFFFAOYSA-N ClC1=CC2=C(N=CNS2(=O)=O)C=C1S(N)(=O)=O Chemical compound ClC1=CC2=C(N=CNS2(=O)=O)C=C1S(N)(=O)=O AJTSGHFOJGUPKV-UHFFFAOYSA-N 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 239000002202 Polyethylene glycol Substances 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 239000003377 acid catalyst Substances 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
• 238000005915 ammonolysis reaction Methods 0.000 description 1
• 239000002246 antineoplastic agent Substances 0.000 description 1
• 125000005605 benzo group Chemical group 0.000 description 1
• 150000007658 benzothiadiazines Chemical class 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 229910052794 bromium Inorganic materials 0.000 description 1
• 239000002775 capsule Substances 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 229940127089 cytotoxic agent Drugs 0.000 description 1
• 239000002934 diuretic Substances 0.000 description 1
• 230000001882 diuretic effect Effects 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 230000001452 natriuretic effect Effects 0.000 description 1
• 229910052757 nitrogen Inorganic materials 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 230000036647 reaction Effects 0.000 description 1
• 238000007363 ring formation reaction Methods 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 238000002211 ultraviolet spectrum Methods 0.000 description 1