DE1670736A1 - Verfahren zur Herstellung von Arylsulfonylsemicarbaziden - Google Patents
Verfahren zur Herstellung von ArylsulfonylsemicarbazidenInfo
- Publication number
- DE1670736A1 DE1670736A1 DE19661670736 DE1670736A DE1670736A1 DE 1670736 A1 DE1670736 A1 DE 1670736A1 DE 19661670736 DE19661670736 DE 19661670736 DE 1670736 A DE1670736 A DE 1670736A DE 1670736 A1 DE1670736 A1 DE 1670736A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- general formula
- alkoxy
- halogen
- acylamino
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 sulfonamide alkali salt Chemical class 0.000 claims description 10
- 125000004442 acylamino group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KPUSZZFAYGWAHZ-UHFFFAOYSA-N 3-azabicyclo[2.2.2]octane Chemical compound C1CC2CCC1NC2 KPUSZZFAYGWAHZ-UHFFFAOYSA-N 0.000 description 1
- JGHDVROWMPBQSR-UHFFFAOYSA-N 4-chloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=C(S(=O)(=O)N=C=O)C=C1 JGHDVROWMPBQSR-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/06—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing isoquinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0050003 | 1966-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1670736A1 true DE1670736A1 (de) | 1970-12-23 |
Family
ID=7103453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661670736 Pending DE1670736A1 (de) | 1966-08-22 | 1966-08-22 | Verfahren zur Herstellung von Arylsulfonylsemicarbaziden |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3764605A (enExample) |
| AT (1) | AT275542B (enExample) |
| BE (1) | BE702903A (enExample) |
| CH (1) | CH487860A (enExample) |
| DE (1) | DE1670736A1 (enExample) |
| DK (1) | DK119830B (enExample) |
| ES (2) | ES344342A1 (enExample) |
| FI (1) | FI45659C (enExample) |
| FR (1) | FR7050M (enExample) |
| GB (1) | GB1199758A (enExample) |
| IL (1) | IL28504A (enExample) |
| NL (1) | NL6711508A (enExample) |
| NO (1) | NO123429B (enExample) |
| SE (1) | SE330698B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443243A (en) * | 1981-07-16 | 1984-04-17 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N-triazinylureas |
| JP2000169474A (ja) * | 1998-12-07 | 2000-06-20 | Kotobuki Seiyaku Kk | イソキヌクリジン誘導体及びその製造方法並びにこれを含有する高コレステロール血症治療剤 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2075359A (en) * | 1930-10-16 | 1937-03-30 | Du Pont | Insecticide |
| US1915334A (en) * | 1930-10-16 | 1933-06-27 | Du Pont | Fluosilicate of organic heterocyclic bases and process of making it |
| DE1191826B (de) * | 1963-09-03 | 1965-04-29 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung neuer Benzolsulfonylsemicarbazide und ihrer Salze |
-
1966
- 1966-08-22 DE DE19661670736 patent/DE1670736A1/de active Pending
-
1967
- 1967-08-07 CH CH1108567A patent/CH487860A/de not_active IP Right Cessation
- 1967-08-15 IL IL28504A patent/IL28504A/en unknown
- 1967-08-16 NO NO169387A patent/NO123429B/no unknown
- 1967-08-16 DK DK416467AA patent/DK119830B/da unknown
- 1967-08-17 US US00661198A patent/US3764605A/en not_active Expired - Lifetime
- 1967-08-18 FI FI672219A patent/FI45659C/fi active
- 1967-08-21 NL NL6711508A patent/NL6711508A/xx unknown
- 1967-08-21 GB GB38460/67A patent/GB1199758A/en not_active Expired
- 1967-08-21 BE BE702903D patent/BE702903A/xx unknown
- 1967-08-22 ES ES344342A patent/ES344342A1/es not_active Expired
- 1967-08-22 SE SE11749/67A patent/SE330698B/xx unknown
- 1967-08-22 AT AT772767A patent/AT275542B/de active
- 1967-09-29 ES ES345565A patent/ES345565A1/es not_active Expired
- 1967-11-21 FR FR129107A patent/FR7050M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES344342A1 (es) | 1969-04-16 |
| GB1199758A (en) | 1970-07-22 |
| SE330698B (enExample) | 1970-11-30 |
| AT275542B (de) | 1969-10-27 |
| BE702903A (enExample) | 1968-02-21 |
| ES345565A1 (es) | 1969-04-16 |
| IL28504A (en) | 1971-10-20 |
| NL6711508A (enExample) | 1968-02-23 |
| US3764605A (en) | 1973-10-09 |
| FR7050M (enExample) | 1969-06-16 |
| CH487860A (de) | 1970-03-31 |
| FI45659B (enExample) | 1972-05-02 |
| NO123429B (enExample) | 1971-11-15 |
| DK119830B (da) | 1971-03-01 |
| FI45659C (fi) | 1972-08-10 |
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