CH407135A - Verfahren zur Herstellung von 1,2,4-Benzothiadiazin-1,1-dioxyden - Google Patents
Verfahren zur Herstellung von 1,2,4-Benzothiadiazin-1,1-dioxydenInfo
- Publication number
- CH407135A CH407135A CH422462A CH422462A CH407135A CH 407135 A CH407135 A CH 407135A CH 422462 A CH422462 A CH 422462A CH 422462 A CH422462 A CH 422462A CH 407135 A CH407135 A CH 407135A
- Authority
- CH
- Switzerland
- Prior art keywords
- benzothiadiazine
- disulfamylaniline
- sulfamyl
- dioxide
- chloral
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 claims description 10
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 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 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000011698 potassium fluoride Substances 0.000 claims description 4
- 235000003270 potassium fluoride Nutrition 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- KRVABEGPNKGLOT-UHFFFAOYSA-N 4-amino-6-(trifluoromethyl)benzene-1,3-disulfonamide Chemical compound NC1=CC(C(F)(F)F)=C(S(N)(=O)=O)C=C1S(N)(=O)=O KRVABEGPNKGLOT-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- RGUQWGXAYZNLMI-UHFFFAOYSA-N flumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O RGUQWGXAYZNLMI-UHFFFAOYSA-N 0.000 claims description 2
- QLGJNQICDRXXGG-UHFFFAOYSA-N (disulfamoylamino)benzene Chemical class NS(=O)(=O)N(S(N)(=O)=O)C1=CC=CC=C1 QLGJNQICDRXXGG-UHFFFAOYSA-N 0.000 claims 1
- -1 disulfamylaniline compound Chemical class 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical class CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 2
- 229960002327 chloral hydrate Drugs 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- CGVXNZNOSZFBCD-UHFFFAOYSA-N 1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound N1=CNS(=O)(=O)C2=CC(S(=O)(=O)N)=CC=C21 CGVXNZNOSZFBCD-UHFFFAOYSA-N 0.000 description 1
- DLHWKJDYXPNWAI-UHFFFAOYSA-N 2,2,2-trichloro-1-ethoxyethanol Chemical compound CCOC(O)C(Cl)(Cl)Cl DLHWKJDYXPNWAI-UHFFFAOYSA-N 0.000 description 1
- QRKDOAWSBBGNLE-UHFFFAOYSA-N 2h-1,2,4-benzothiadiazine Chemical compound C1=CC=C2N=CNSC2=C1 QRKDOAWSBBGNLE-UHFFFAOYSA-N 0.000 description 1
- YRXAPDMJILMLSU-UHFFFAOYSA-N 4-amino-6-bromobenzene-1,3-disulfonamide Chemical compound NC1=CC(Br)=C(S(N)(=O)=O)C=C1S(N)(=O)=O YRXAPDMJILMLSU-UHFFFAOYSA-N 0.000 description 1
- GEZVQOGNDGUDNU-UHFFFAOYSA-N 4-amino-6-chloro-1-n-methylbenzene-1,3-disulfonamide Chemical compound CNS(=O)(=O)C1=CC(S(N)(=O)=O)=C(N)C=C1Cl GEZVQOGNDGUDNU-UHFFFAOYSA-N 0.000 description 1
- BIZYKPCIWRGRPJ-UHFFFAOYSA-N 4-amino-6-chloro-5-methylbenzene-1,3-disulfonamide Chemical compound CC1=C(N)C(S(N)(=O)=O)=CC(S(N)(=O)=O)=C1Cl BIZYKPCIWRGRPJ-UHFFFAOYSA-N 0.000 description 1
- OBRVGHAGEZLLGG-UHFFFAOYSA-N 4-amino-6-fluorobenzene-1,3-disulfonamide Chemical compound FC=1C(=CC(=C(N)C1)S(N)(=O)=O)S(N)(=O)=O OBRVGHAGEZLLGG-UHFFFAOYSA-N 0.000 description 1
- IJHBKNKFSJLONU-UHFFFAOYSA-N 4-amino-6-methoxybenzene-1,3-disulfonamide Chemical compound COC1=CC(N)=C(S(N)(=O)=O)C=C1S(N)(=O)=O IJHBKNKFSJLONU-UHFFFAOYSA-N 0.000 description 1
- JGFQDYAUPNZBMU-UHFFFAOYSA-N 4-amino-6-methylbenzene-1,3-disulfonamide Chemical compound CC1=CC(N)=C(S(N)(=O)=O)C=C1S(N)(=O)=O JGFQDYAUPNZBMU-UHFFFAOYSA-N 0.000 description 1
- IBNXNSNZXLVXSJ-UHFFFAOYSA-N 4-amino-6-nitrobenzene-1,3-disulfonamide Chemical compound NC1=CC([N+]([O-])=O)=C(S(N)(=O)=O)C=C1S(N)(=O)=O IBNXNSNZXLVXSJ-UHFFFAOYSA-N 0.000 description 1
- BOZSDDFQWJUBNG-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1S(N)(=O)=O BOZSDDFQWJUBNG-UHFFFAOYSA-N 0.000 description 1
- BBNGVMNBBLPZIR-UHFFFAOYSA-N 4h-1$l^{6},2,4-benzothiadiazine 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)N=CNC2=C1 BBNGVMNBBLPZIR-UHFFFAOYSA-N 0.000 description 1
- CAAKQRQFOMKFGK-UHFFFAOYSA-N 6-bromo-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(Br)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O CAAKQRQFOMKFGK-UHFFFAOYSA-N 0.000 description 1
- UNUUPKIWWPPKGU-UHFFFAOYSA-N 6-chloro-5-methyl-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound N1C=NS(=O)(=O)C2=C1C(C)=C(Cl)C(S(N)(=O)=O)=C2 UNUUPKIWWPPKGU-UHFFFAOYSA-N 0.000 description 1
- YYWLICGCICEVGT-UHFFFAOYSA-N 6-fluoro-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound C1=C(F)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O YYWLICGCICEVGT-UHFFFAOYSA-N 0.000 description 1
- OGXNOHZPFAKPAC-UHFFFAOYSA-N 6-methoxy-1,1-dioxo-4h-1$l^{6},2,4-benzothiadiazine-7-sulfonamide Chemical compound N1C=NS(=O)(=O)C2=C1C=C(OC)C(S(N)(=O)=O)=C2 OGXNOHZPFAKPAC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical group C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10133261A | 1961-04-07 | 1961-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH407135A true CH407135A (de) | 1966-02-15 |
Family
ID=22284090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH422462A CH407135A (de) | 1961-04-07 | 1962-04-06 | Verfahren zur Herstellung von 1,2,4-Benzothiadiazin-1,1-dioxyden |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH407135A (da) |
| DK (1) | DK106332C (da) |
| FI (1) | FI43599B (da) |
| SE (1) | SE302612B (da) |
-
1962
- 1962-03-30 FI FI0689/62A patent/FI43599B/fi active
- 1962-04-05 DK DK157662AA patent/DK106332C/da active
- 1962-04-06 SE SE3855/62A patent/SE302612B/xx unknown
- 1962-04-06 CH CH422462A patent/CH407135A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE302612B (da) | 1968-07-29 |
| FI43599B (da) | 1971-02-01 |
| DK106332C (da) | 1967-01-23 |
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