IE791789L - Preparation of 1,2,3-thiadiazol-5-yl ureas - Google Patents
Preparation of 1,2,3-thiadiazol-5-yl ureasInfo
- Publication number
- IE791789L IE791789L IE791789A IE178979A IE791789L IE 791789 L IE791789 L IE 791789L IE 791789 A IE791789 A IE 791789A IE 178979 A IE178979 A IE 178979A IE 791789 L IE791789 L IE 791789L
- Authority
- IE
- Ireland
- Prior art keywords
- ureas
- optionally substituted
- alkyl
- oxygen
- image
- Prior art date
Links
- -1 1,2,3-thiadiazol-5-yl ureas Chemical class 0.000 title abstract 3
- 235000013877 carbamide Nutrition 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- PVGHNTXQMCYYGF-UHFFFAOYSA-N thiadiazol-5-amine Chemical compound NC1=CN=NS1 PVGHNTXQMCYYGF-UHFFFAOYSA-N 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 150000003672 ureas Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1,2,3-Thiadiazol-5-yl ureas of the formula:- <IMAGE> wherein R1 represents hydrogen or alkyl optionally interrupted by one or more oxygen and/or sulphur atoms, and R2 represents alkyl optionally interrupted by one or more oxygen and/or sulphur atoms, or a cycloalkyl radical optionally substituted by one or more alkyl radicals, an aromatic hydrocarbon radical optionally substituted by one or more substituents selected from alkyl, halogen, alkylthio, alkoxy, trifluoromethyl and nitro, or an optionally substituted N-containing heterocyclic radical or NR1R2 represents morpholino, piperidino or pyrrolidino, are prepared by reacting a compounds:- <IMAGE> with amines (R1-NH-R2) in inert organic solvents. Preferably the compound II is formed in the reaction mixture. The process of the invention makes it possible to prepare the ureas in a safe and technically simple manner in virtually quantitative yields and good purity. Previously the preparations required the use of 5-amino-1,2,3- thiadiazole which is not easily obtained and is not completely harmless.
[GB2031889A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782841825 DE2841825A1 (en) | 1978-09-22 | 1978-09-22 | METHOD FOR THE PRODUCTION OF 1,2,3-THIADIAZOL-5-YL UREA |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE791789L true IE791789L (en) | 1980-03-22 |
| IE48944B1 IE48944B1 (en) | 1985-06-26 |
Family
ID=6050477
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1789/79A IE48944B1 (en) | 1978-09-22 | 1979-09-21 | Process for the preparation of 1,2,3-thiadiazol-5-yl ureas |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5545683A (en) |
| AR (1) | AR223349A1 (en) |
| AT (1) | AT373593B (en) |
| AU (1) | AU533137B2 (en) |
| BE (1) | BE878925A (en) |
| BG (1) | BG30930A3 (en) |
| BR (1) | BR7905614A (en) |
| CA (1) | CA1131224A (en) |
| CH (1) | CH641792A5 (en) |
| CS (1) | CS209936B2 (en) |
| DD (1) | DD146184A5 (en) |
| DE (1) | DE2841825A1 (en) |
| DK (1) | DK361579A (en) |
| EG (1) | EG14167A (en) |
| ES (1) | ES483788A1 (en) |
| FI (1) | FI69838C (en) |
| FR (1) | FR2436783A1 (en) |
| GB (1) | GB2031889B (en) |
| GR (1) | GR73092B (en) |
| HU (1) | HU182999B (en) |
| IE (1) | IE48944B1 (en) |
| IL (1) | IL58274A (en) |
| IT (1) | IT1123731B (en) |
| LU (1) | LU81704A1 (en) |
| NL (1) | NL7905355A (en) |
| NZ (1) | NZ191603A (en) |
| PH (1) | PH15388A (en) |
| PL (1) | PL123956B1 (en) |
| PT (1) | PT70178A (en) |
| RO (1) | RO77754A (en) |
| SE (1) | SE435376B (en) |
| SU (1) | SU921466A3 (en) |
| TR (1) | TR20895A (en) |
| YU (1) | YU40759B (en) |
| ZA (1) | ZA794722B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2909991A1 (en) * | 1979-03-12 | 1980-10-02 | Schering Ag | 1,2,3-THIADIAZOL-5-CARBONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS, AND THEIR CONTAINING AGENTS WITH HERBICIDAL AND GROWTH REGULATORY AND FUNGICIDAL EFFECT |
| JPS55150238U (en) * | 1980-04-03 | 1980-10-29 | ||
| DE3139506A1 (en) * | 1981-10-01 | 1983-04-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 1,2,3-THIADIAZOL-5-YL-UREA DERIVATIVES, METHOD FOR THE PRODUCTION OF THESE COMPOUNDS AND THEIR CONTAINING AGENTS WITH GROWTH REGULATIVE AND DEFOLIATING EFFECT |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD103124A5 (en) | 1972-03-23 | 1974-01-12 | ||
| DE2636994C2 (en) | 1976-08-13 | 1984-10-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | Process for the preparation of 5-amino-1,2,3-thiadiazole |
-
1978
- 1978-09-22 DE DE19782841825 patent/DE2841825A1/en not_active Withdrawn
-
1979
- 1979-07-09 NL NL7905355A patent/NL7905355A/en not_active Application Discontinuation
- 1979-08-20 YU YU2027/79A patent/YU40759B/en unknown
- 1979-08-29 DK DK361579A patent/DK361579A/en not_active Application Discontinuation
- 1979-08-31 ES ES483788A patent/ES483788A1/en not_active Expired
- 1979-08-31 BR BR7905614A patent/BR7905614A/en unknown
- 1979-09-06 ZA ZA00794722A patent/ZA794722B/en unknown
- 1979-09-06 FI FI792770A patent/FI69838C/en not_active IP Right Cessation
- 1979-09-11 CA CA335,363A patent/CA1131224A/en not_active Expired
- 1979-09-14 PT PT70178A patent/PT70178A/en unknown
- 1979-09-14 BG BG044862A patent/BG30930A3/en unknown
- 1979-09-17 TR TR20895A patent/TR20895A/en unknown
- 1979-09-18 EG EG555/79A patent/EG14167A/en active
- 1979-09-18 NZ NZ191603A patent/NZ191603A/en unknown
- 1979-09-19 IL IL58274A patent/IL58274A/en unknown
- 1979-09-19 DD DD215645A patent/DD146184A5/en unknown
- 1979-09-20 PL PL1979218429A patent/PL123956B1/en unknown
- 1979-09-20 IT IT25880/79A patent/IT1123731B/en active
- 1979-09-20 LU LU81704A patent/LU81704A1/en unknown
- 1979-09-20 GR GR60083A patent/GR73092B/el unknown
- 1979-09-20 CH CH850479A patent/CH641792A5/en not_active IP Right Cessation
- 1979-09-20 PH PH23049A patent/PH15388A/en unknown
- 1979-09-20 SU SU792811707A patent/SU921466A3/en active
- 1979-09-21 AT AT0622779A patent/AT373593B/en not_active IP Right Cessation
- 1979-09-21 RO RO7998731A patent/RO77754A/en unknown
- 1979-09-21 CS CS796380A patent/CS209936B2/en unknown
- 1979-09-21 BE BE0/197257A patent/BE878925A/en not_active IP Right Cessation
- 1979-09-21 JP JP12093079A patent/JPS5545683A/en active Pending
- 1979-09-21 SE SE7907841A patent/SE435376B/en not_active IP Right Cessation
- 1979-09-21 AR AR278157A patent/AR223349A1/en active
- 1979-09-21 HU HU79SCHE691A patent/HU182999B/en unknown
- 1979-09-21 AU AU51075/79A patent/AU533137B2/en not_active Ceased
- 1979-09-21 GB GB7932815A patent/GB2031889B/en not_active Expired
- 1979-09-21 IE IE1789/79A patent/IE48944B1/en unknown
- 1979-09-24 FR FR7923681A patent/FR2436783A1/en active Granted
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