SU448641A3 - Способ получени бензолсульфонилмочевины - Google Patents
Способ получени бензолсульфонилмочевиныInfo
- Publication number
- SU448641A3 SU448641A3 SU1623403A SU1623403A SU448641A3 SU 448641 A3 SU448641 A3 SU 448641A3 SU 1623403 A SU1623403 A SU 1623403A SU 1623403 A SU1623403 A SU 1623403A SU 448641 A3 SU448641 A3 SU 448641A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ethyl
- cycloheptylurea
- chlorobenzamido
- methoxy
- benzenesulfonyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 3
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 title description 2
- -1 methoxymethoxy, ethoxymethoxy Chemical group 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000155 melt Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- SZGLLXJFYCJRPP-UHFFFAOYSA-N cycloheptylurea Chemical compound NC(=O)NC1CCCCCC1 SZGLLXJFYCJRPP-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000002253 acid Substances 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- JCNLHDHXQVZQAM-UHFFFAOYSA-N isocyanatocycloheptane Chemical compound O=C=NC1CCCCCC1 JCNLHDHXQVZQAM-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 229940058172 ethylbenzene Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KBGBYEKVPXJLNE-UHFFFAOYSA-N 1-(benzenesulfonyl)-1-cycloheptylurea Chemical compound C1(=CC=CC=C1)S(=O)(=O)N(C(=O)N)C1CCCCCC1 KBGBYEKVPXJLNE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000256856 Vespidae Species 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical compound OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LSDFDZGBOGURGN-UHFFFAOYSA-N ethylbenzene sulfamide Chemical compound S(=O)(=O)(N)N.C(C)C1=CC=CC=C1 LSDFDZGBOGURGN-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thermally Actuated Switches (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0051164 | 1967-01-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU448641A3 true SU448641A3 (ru) | 1974-10-30 |
Family
ID=7104389
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1623403A SU448641A3 (ru) | 1967-01-03 | 1968-01-02 | Способ получени бензолсульфонилмочевины |
| SU1406183A SU453829A3 (ru) | 1967-01-03 | 1968-01-02 | Способ получения замещенной бензол сульфонилмочевины |
| SU1406180A SU468402A3 (ru) | 1967-01-03 | 1968-01-02 | Способ получени замещенной бензолсульфонилмочевины |
| SU1207929A SU366605A3 (enrdf_load_stackoverflow) | 1967-01-03 | 1968-01-02 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1406183A SU453829A3 (ru) | 1967-01-03 | 1968-01-02 | Способ получения замещенной бензол сульфонилмочевины |
| SU1406180A SU468402A3 (ru) | 1967-01-03 | 1968-01-02 | Способ получени замещенной бензолсульфонилмочевины |
| SU1207929A SU366605A3 (enrdf_load_stackoverflow) | 1967-01-03 | 1968-01-02 |
Country Status (21)
-
1967
- 1967-01-03 DE DE1618333A patent/DE1618333C3/de not_active Expired
- 1967-12-14 DK DK627167AA patent/DK123865B/da unknown
- 1967-12-18 IS IS1711A patent/IS897B6/is unknown
- 1967-12-20 MC MC740A patent/MC698A1/xx unknown
- 1967-12-20 LU LU55140D patent/LU55140A1/xx unknown
- 1967-12-21 IL IL29182A patent/IL29182A/xx unknown
- 1967-12-22 CH CH548470A patent/CH567464A5/xx not_active IP Right Cessation
- 1967-12-22 CH CH1805167A patent/CH524579A/de not_active IP Right Cessation
- 1967-12-22 CH CH548270A patent/CH566973A5/xx not_active IP Right Cessation
- 1967-12-22 CH CH548370A patent/CH566974A5/xx not_active IP Right Cessation
- 1967-12-22 CH CH548570A patent/CH566975A5/xx not_active IP Right Cessation
- 1967-12-28 OA OA53137A patent/OA03383A/xx unknown
- 1967-12-28 NO NO171182A patent/NO123385B/no unknown
- 1967-12-29 ES ES348773A patent/ES348773A1/es not_active Expired
- 1967-12-29 NL NL6717808A patent/NL6717808A/xx unknown
- 1967-12-30 FI FI673527A patent/FI49157C/fi active
-
1968
- 1968-01-02 FR FR1559029D patent/FR1559029A/fr not_active Expired
- 1968-01-02 CS CS30*YA patent/CS161702B2/cs unknown
- 1968-01-02 SU SU1623403A patent/SU448641A3/ru active
- 1968-01-02 SU SU1406183A patent/SU453829A3/ru active
- 1968-01-02 SU SU1406180A patent/SU468402A3/ru active
- 1968-01-02 AT AT968*BA patent/AT327935B/de not_active IP Right Cessation
- 1968-01-02 SU SU1207929A patent/SU366605A3/ru active
- 1968-01-03 GB GB447/68A patent/GB1205322A/en not_active Expired
- 1968-01-03 SE SE00039/68A patent/SE339222B/xx unknown
- 1968-01-03 BE BE708917D patent/BE708917A/xx unknown
- 1968-03-29 FR FR146589A patent/FR8386M/fr not_active Expired
-
1969
- 1969-04-29 ES ES366601A patent/ES366601A1/es not_active Expired
- 1969-05-21 DK DK275669AA patent/DK122722B/da unknown
-
1971
- 1971-04-22 CY CY58671A patent/CY586A/xx unknown
- 1971-12-30 MY MY110/71A patent/MY7100110A/xx unknown
-
1974
- 1974-03-22 CH CH1805167A patent/CH593249A5/xx not_active IP Right Cessation
- 1974-12-22 CH CH554174A patent/CH592614A5/xx not_active IP Right Cessation
Also Published As
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