JPS58194881A - ７‐スルホンアミドチオクロマン―１，１‐ジオン類の改良製法 - Google Patents
７‐スルホンアミドチオクロマン―１，１‐ジオン類の改良製法Info
- Publication number
- JPS58194881A JPS58194881A JP7661282A JP7661282A JPS58194881A JP S58194881 A JPS58194881 A JP S58194881A JP 7661282 A JP7661282 A JP 7661282A JP 7661282 A JP7661282 A JP 7661282A JP S58194881 A JPS58194881 A JP S58194881A
- Authority
- JP
- Japan
- Prior art keywords
- diones
- thiochroman
- reaction
- dione
- dichloromethane
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- 229940124530 sulfonamide Drugs 0.000 title description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 87
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
- AMFFYPOSQJWMKB-UHFFFAOYSA-N 1,1-dioxo-3,4-dihydro-2h-thiochromene-7-sulfonyl chloride Chemical class C1CCS(=O)(=O)C2=CC(S(=O)(=O)Cl)=CC=C21 AMFFYPOSQJWMKB-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 32
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 25
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 22
- TVAXADJKLPDCJU-UHFFFAOYSA-N 3,4-dihydro-2h-thiochromene 1,1-dioxide Chemical class C1=CC=C2S(=O)(=O)CCCC2=C1 TVAXADJKLPDCJU-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000004448 titration Methods 0.000 description 8
- 238000007796 conventional method Methods 0.000 description 7
- 241000551547 Dione <red algae> Species 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- JSNJMRWCUWQHKF-UHFFFAOYSA-N 6-methyl-1,1-dioxo-3,4-dihydro-2h-thiochromene-7-sulfonyl chloride Chemical compound C1CCS(=O)(=O)C2=C1C=C(C)C(S(Cl)(=O)=O)=C2 JSNJMRWCUWQHKF-UHFFFAOYSA-N 0.000 description 5
- WSZWAAAVGHPCNK-UHFFFAOYSA-N 6-methyl-3,4-dihydro-2h-thiochromene 1,1-dioxide Chemical compound C1CCS(=O)(=O)C=2C1=CC(C)=CC=2 WSZWAAAVGHPCNK-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000006277 sulfonation reaction Methods 0.000 description 5
- 238000005979 thermal decomposition reaction Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 2
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007112 amidation reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- DEVZLAURCKUABI-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-thiochromene 1,1-dioxide Chemical compound C1CCS(=O)(=O)C=2C1=CC(Cl)=CC=2 DEVZLAURCKUABI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- -1 chlorosulfonylthiochroman-1,1-dione Chemical compound 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7661282A JPS58194881A (ja) | 1982-05-10 | 1982-05-10 | ７‐スルホンアミドチオクロマン―１，１‐ジオン類の改良製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7661282A JPS58194881A (ja) | 1982-05-10 | 1982-05-10 | ７‐スルホンアミドチオクロマン―１，１‐ジオン類の改良製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58194881A true JPS58194881A (ja) | 1983-11-12 |
| JPH0257556B2 JPH0257556B2 (enrdf_load_stackoverflow) | 1990-12-05 |
Family
ID=13610159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7661282A Granted JPS58194881A (ja) | 1982-05-10 | 1982-05-10 | ７‐スルホンアミドチオクロマン―１，１‐ジオン類の改良製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58194881A (enrdf_load_stackoverflow) |
-
1982
- 1982-05-10 JP JP7661282A patent/JPS58194881A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0257556B2 (enrdf_load_stackoverflow) | 1990-12-05 |
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