SU453829A3 - Способ получения замещенной бензол сульфонилмочевины - Google Patents
Способ получения замещенной бензол сульфонилмочевиныInfo
- Publication number
- SU453829A3 SU453829A3 SU1406183A SU1406183A SU453829A3 SU 453829 A3 SU453829 A3 SU 453829A3 SU 1406183 A SU1406183 A SU 1406183A SU 1406183 A SU1406183 A SU 1406183A SU 453829 A3 SU453829 A3 SU 453829A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ethyl
- benzenesulfonyl
- methoxy
- urea
- sulphonylmolovie
- Prior art date
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title description 4
- 238000000034 method Methods 0.000 title description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 7
- -1 formyl chloride acyl chloride Chemical class 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SZGLLXJFYCJRPP-UHFFFAOYSA-N cycloheptylurea Chemical compound NC(=O)NC1CCCCCC1 SZGLLXJFYCJRPP-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- KUIYILOSSGJKHZ-UHFFFAOYSA-N 1,3-bis(benzenesulfonyl)urea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NS(=O)(=O)C1=CC=CC=C1 KUIYILOSSGJKHZ-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
- MOIQCUSEEYCGON-UHFFFAOYSA-N 1-sulfonylethyl N-methylcarbamate Chemical compound S(=O)(=O)=C(OC(NC)=O)C MOIQCUSEEYCGON-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- HHQBVLHGPLRNHL-UHFFFAOYSA-N C(C)(=O)[O-].C1(CCCCCC1)[NH3+] Chemical compound C(C)(=O)[O-].C1(CCCCCC1)[NH3+] HHQBVLHGPLRNHL-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 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
- NQYFSRNBBUXTIQ-UHFFFAOYSA-N benzylsulfonylurea Chemical compound NC(=O)NS(=O)(=O)CC1=CC=CC=C1 NQYFSRNBBUXTIQ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XNBKKRFABABBPM-UHFFFAOYSA-N n,n-diphenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C1=CC=CC=C1 XNBKKRFABABBPM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000008096 xylene Substances 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 |
|---|---|
| SU453829A3 true SU453829A3 (ru) | 1974-12-15 |
Family
ID=7104389
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1207929A SU366605A3 (enrdf_load_stackoverflow) | 1967-01-03 | 1968-01-02 | |
| SU1406183A SU453829A3 (ru) | 1967-01-03 | 1968-01-02 | Способ получения замещенной бензол сульфонилмочевины |
| SU1623403A SU448641A3 (ru) | 1967-01-03 | 1968-01-02 | Способ получени бензолсульфонилмочевины |
| SU1406180A SU468402A3 (ru) | 1967-01-03 | 1968-01-02 | Способ получени замещенной бензолсульфонилмочевины |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1207929A SU366605A3 (enrdf_load_stackoverflow) | 1967-01-03 | 1968-01-02 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1623403A SU448641A3 (ru) | 1967-01-03 | 1968-01-02 | Способ получени бензолсульфонилмочевины |
| SU1406180A SU468402A3 (ru) | 1967-01-03 | 1968-01-02 | Способ получени замещенной бензолсульфонилмочевины |
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 LU LU55140D patent/LU55140A1/xx unknown
- 1967-12-20 MC MC740A patent/MC698A1/xx unknown
- 1967-12-21 IL IL29182A patent/IL29182A/xx unknown
- 1967-12-22 CH CH548570A patent/CH566975A5/xx not_active IP Right Cessation
- 1967-12-22 CH CH548470A patent/CH567464A5/xx not_active IP Right Cessation
- 1967-12-22 CH CH548270A patent/CH566973A5/xx not_active IP Right Cessation
- 1967-12-22 CH CH1805167A patent/CH524579A/de not_active IP Right Cessation
- 1967-12-22 CH CH548370A patent/CH566974A5/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 NL NL6717808A patent/NL6717808A/xx unknown
- 1967-12-29 ES ES348773A patent/ES348773A1/es not_active Expired
- 1967-12-30 FI FI673527A patent/FI49157C/fi active
-
1968
- 1968-01-02 SU SU1207929A patent/SU366605A3/ru active
- 1968-01-02 CS CS30*YA patent/CS161702B2/cs unknown
- 1968-01-02 FR FR1559029D patent/FR1559029A/fr not_active Expired
- 1968-01-02 SU SU1406183A patent/SU453829A3/ru active
- 1968-01-02 AT AT968*BA patent/AT327935B/de not_active IP Right Cessation
- 1968-01-02 SU SU1623403A patent/SU448641A3/ru active
- 1968-01-02 SU SU1406180A patent/SU468402A3/ru active
- 1968-01-03 SE SE00039/68A patent/SE339222B/xx unknown
- 1968-01-03 BE BE708917D patent/BE708917A/xx unknown
- 1968-01-03 GB GB447/68A patent/GB1205322A/en not_active Expired
- 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
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