SU475766A3 - Способ получени замещенной бензолсульфонилмочевины - Google Patents
Способ получени замещенной бензолсульфонилмочевиныInfo
- Publication number
- SU475766A3 SU475766A3 SU1460550A SU1460550A SU475766A3 SU 475766 A3 SU475766 A3 SU 475766A3 SU 1460550 A SU1460550 A SU 1460550A SU 1460550 A SU1460550 A SU 1460550A SU 475766 A3 SU475766 A3 SU 475766A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ethyl
- chlorobenzamido
- benzenesulfonyl
- methoxy
- alkyl
- Prior art date
Links
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 title description 2
- 238000000034 method Methods 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- -1 benzenesulfonyl urea ethers Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- AHWQFDVYWIQZGC-UHFFFAOYSA-N CCC1=C(C=CC=C1S(=O)(=O)Cl)NC(=O)C2=C(C=CC(=C2)Cl)OC Chemical compound CCC1=C(C=CC=C1S(=O)(=O)Cl)NC(=O)C2=C(C=CC(=C2)Cl)OC AHWQFDVYWIQZGC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- FZHUSKDYYVARES-UHFFFAOYSA-N cyclohexen-1-ylthiourea Chemical compound NC(=S)NC1=CCCCC1 FZHUSKDYYVARES-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- DKSBQEIJEJFTAW-UHFFFAOYSA-N methanol N-methylformamide Chemical compound CO.CNC=O DKSBQEIJEJFTAW-UHFFFAOYSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical compound O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681793111 DE1793111C3 (de) | 1968-08-02 | Acylaminoäthylbenzolsulfonyl-delta hoch 2-cyclohexenyl-harnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU475766A3 true SU475766A3 (ru) | 1975-06-30 |
Family
ID=5707579
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1460550A SU475766A3 (ru) | 1968-08-02 | 1969-08-01 | Способ получени замещенной бензолсульфонилмочевины |
| SU1620867A SU420172A3 (enExample) | 1968-08-02 | 1969-08-01 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1620867A SU420172A3 (enExample) | 1968-08-02 | 1969-08-01 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3790630A (enExample) |
| AR (4) | AR192862A1 (enExample) |
| AT (3) | AT321929B (enExample) |
| BE (1) | BE737061A (enExample) |
| CA (1) | CA954136A (enExample) |
| CH (1) | CH520119A (enExample) |
| CS (8) | CS163192B2 (enExample) |
| CY (1) | CY629A (enExample) |
| DK (1) | DK125642C (enExample) |
| ES (1) | ES370075A1 (enExample) |
| FI (1) | FI50117C (enExample) |
| FR (1) | FR2014957A1 (enExample) |
| GB (1) | GB1233354A (enExample) |
| IE (1) | IE33498B1 (enExample) |
| IL (1) | IL32731A (enExample) |
| LU (1) | LU59170A1 (enExample) |
| MY (1) | MY7200082A (enExample) |
| NL (1) | NL6911626A (enExample) |
| NO (1) | NO127707B (enExample) |
| OA (1) | OA03367A (enExample) |
| PL (1) | PL80151B1 (enExample) |
| SE (1) | SE363094B (enExample) |
| SU (2) | SU475766A3 (enExample) |
| ZM (1) | ZM12469A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4028046A1 (de) * | 1990-09-05 | 1992-03-12 | Bayer Ag | Arzneimittel enthaltend substituierte 2-cyclohexen-1-yl-amin-derivate und ihre verwendung zur bekaempfung von krankheiten |
-
1969
- 1969-02-14 GB GB821869A patent/GB1233354A/en not_active Expired
- 1969-07-24 IE IE1031/69A patent/IE33498B1/xx unknown
- 1969-07-25 LU LU59170D patent/LU59170A1/xx unknown
- 1969-07-28 US US00845497A patent/US3790630A/en not_active Expired - Lifetime
- 1969-07-28 FI FI692234A patent/FI50117C/fi active
- 1969-07-28 OA OA53688A patent/OA03367A/xx unknown
- 1969-07-30 IL IL32731A patent/IL32731A/xx unknown
- 1969-07-30 CH CH1161169A patent/CH520119A/de not_active IP Right Cessation
- 1969-07-30 NL NL6911626A patent/NL6911626A/xx not_active Application Discontinuation
- 1969-07-30 ES ES370075A patent/ES370075A1/es not_active Expired
- 1969-07-31 NO NO03152/69A patent/NO127707B/no unknown
- 1969-07-31 CA CA058,372A patent/CA954136A/en not_active Expired
- 1969-08-01 DK DK416869A patent/DK125642C/da active
- 1969-08-01 ZM ZM124/69A patent/ZM12469A1/xx unknown
- 1969-08-01 SU SU1460550A patent/SU475766A3/ru active
- 1969-08-01 AT AT998573*1A patent/AT321929B/de not_active IP Right Cessation
- 1969-08-01 AT AT744369A patent/AT318646B/de not_active IP Right Cessation
- 1969-08-01 PL PL1969135169A patent/PL80151B1/pl unknown
- 1969-08-01 AT AT998673*1A patent/AT321928B/de not_active IP Right Cessation
- 1969-08-01 SU SU1620867A patent/SU420172A3/ru active
- 1969-08-01 FR FR6926511A patent/FR2014957A1/fr not_active Withdrawn
- 1969-08-01 SE SE10793/69A patent/SE363094B/xx unknown
- 1969-08-04 CS CS6930*A patent/CS163192B2/cs unknown
- 1969-08-04 CS CS6929*A patent/CS163191B2/cs unknown
- 1969-08-04 BE BE737061D patent/BE737061A/xx unknown
- 1969-08-04 CS CS5397A patent/CS163186B2/cs unknown
- 1969-08-04 CS CS6925*A patent/CS163187B2/cs unknown
- 1969-08-04 CS CS6926*A patent/CS163188B2/cs unknown
- 1969-08-04 CS CS6928*A patent/CS163190B2/cs unknown
- 1969-08-04 CS CS6927*A patent/CS163189B2/cs unknown
- 1969-08-04 CS CS6931*A patent/CS163193B2/cs unknown
-
1970
- 1970-07-21 AR AR230151A patent/AR192862A1/es active
- 1970-07-21 AR AR230148A patent/AR193603A1/es active
-
1972
- 1972-02-12 CY CY62972A patent/CY629A/xx unknown
- 1972-12-30 MY MY82/72A patent/MY7200082A/xx unknown
-
1973
- 1973-04-23 AR AR247644A patent/AR194180A1/es active
- 1973-06-01 AR AR248361A patent/AR194691A1/es active
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