SI9200292B - Nov postopek za pripravo 4-metil-5-(2-kloroetil)-tiazola in njegovih analogov - Google Patents
Nov postopek za pripravo 4-metil-5-(2-kloroetil)-tiazola in njegovih analogov Download PDFInfo
- Publication number
- SI9200292B SI9200292B SI9200292A SI9200292A SI9200292B SI 9200292 B SI9200292 B SI 9200292B SI 9200292 A SI9200292 A SI 9200292A SI 9200292 A SI9200292 A SI 9200292A SI 9200292 B SI9200292 B SI 9200292B
- Authority
- SI
- Slovenia
- Prior art keywords
- chloro
- general formula
- alkyl
- formula
- process according
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/02—Thiocyanates
- C07C331/04—Thiocyanates having sulfur atoms of thiocyanate groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (15)
1 PATENTNI ZAHTEVKI 1. Postopek za pripravo 5-(2-kloro-C2.5-alkil)-4-metil-l,3-tiazolov s splošno formulo I
ch3 (I)/ kjer je R ravna C2-5-alkilna skupina, substituirana z atomom klora v legi 2, in njihovih kislinskih adicijskih soli, označen s tem, da (Al) 3-(2-kloro-C2_5-alkil)-3-tiocianato-2-propanon s splošno formulo IV R - CH - C - CH^ (IV), I SC N 0 kjer je R, kot je definirano zgoraj, presnovimo v organskem topilu s plinastim klorovodikom pri temperaturi v območju od 0° do 100 °C, da dobimo ustrezen 2-kloro-5-(2-kloro-C2.5-alkil)-4-metil-l,3-tiazol s splošno formulo Π Cl- ch3 r—\( (ir), kjer je R, kot je definirano zgoraj, ali (A2) 3-(2-kloro-C2.5-alkil)-3-tiocianato-2-propanon z gornjo formulo IV R CH C tl
SCN O (IV), 2 presnovimo z vodno mineralno kislino, da dobimo ustrezen 5-(2-kloro-C2.5-alkil)-2-hidroksi-4-metil- 1,3-tiazol s splošno formulo III CHi HO· N' Π .A* (III), kjer je R, kot je definirano zgoraj, in tako dobljeno spojino s formulo III presnovimo s halogenimim sredstvom, da dobimo ustrezen 2-kloro-5-(2-kloro-C2.5-alkil)-4-metil-1,3-tiazol z gornjo formulo II, in (B) spojino s splošno forulo II hidrogeniramo v prisotnosti katalizatorja paladija na oglju ali selenovega katalizatorja, ki vsebuje paladij, da dobimo 5-(2-kloro-C2.5-alkil)-4-metil-1,3-tiazol z gornjo splošno formulo I, in v danem primeru (Cl) spojino z gornjo formulo I ali njen hidroklorid pretvorimo v drugo njeno kislinsko adicijsko sol ali (C2) spojino z gornjo formulo I sprostimo iz njene kislinske adicijske soli.
2. Postopek po zahtevku 1, označen s tem, da R stoji za 2-kloroetil.
3. Postopek po enem od zahtevkov 1 do 2, označen s tem, da izvedemo hidrogeniranje v prisotnosti sredstva za vezanje kisline, prednostno v prisotnosti trietilamina.
4. Postopek po enem od zahtevkov 1 do 3, označen s tem, da kot organsko topilo v stopnjah Al in/ali B uporabimo alifatske alkohole, estre maščobnih kislin, nastale z alifatskimi alkoholi, aromatske ogljikovodike in/ali etre z odprto verigo.
5. Postopek po enem od zahtevkov 1 do 4, označen s tem, da izvedemo hidrogeniranje pri ali nad atmosferskim tlakom, vendar največ pri tlaku 0,7 MPa. 3
6. Postopek po enem od zahtevkov 1 do 5, označen s tem, da izvedemo reakcijo sklenitve obroča iz spojin s splošno formulo (TV) v spojine s splošno formulo (Π) v brezvodnih topilih, ki se ne mešajo z vodo in ki ne raztapljajo vode, prednostno v butilacetatu.
7. Postopek po enem od zahtevkov 1 do 6, označen s tem, da je vodna mineralna kislina vodna fosforjeva kislina.
8. Postopek po enem od zahtevkov 1 do 7, označen s tem, da spojine s splošno formulo (IV) presnovimo z vodno mineralno kislino pri temperaturi v območju od 50 °C do 120 °C.
9. Postopek po enem od zahtevkov 1 do 8, označen s tem, da spojine s splošno formulo (III) halogeniramo s fosforilkloridom, fosfoijevim pentakloridom in/ali fosforjevim trikloridom.
10. Postopek po enem od zahtevkov 1 do 9, označen s tem, da halogeniramo spojine s splošno formulo (ΙΠ) v halogeniranem aromatskem topilu.
11. 3-(2-kloro-C2.5-alkil)-3-tiocianato-2-propanom s splošno formulo IV R - CM - C - CHj SCM O (W)t kjer je R ravna C2.5-alkilna skupina, substituirana z atomom klora v legi 2.
12. Spojina po zahtevku 11, označena s tem, da R stoji za 2-kloroetil.
13. Postopek za pripravo 3-(2-kloro-C2.5-alkil)-3-tiocianato-2-propanonov s splošno formulo IV, označen s tem, da 3-kloro-3-(2-kloro-C2.5-alkil)-2-propanon s splošno formulo V 4 R - CH - C - CH^ I - (V), C1 o kjer je R ravna C2-5-alkilna skupina, substituirana z atomom klora v legi 2, presnovimo z anorganskim tiocianatom, prednostno izbranim izmed natrijevega tiocianata, kalijevega tiocianata in amonijevega tiocianata.
14. Postopek po zahtevku 13, označen s tem, da ga izvedemo v prisotnosti topila, kot alifatskih alkoholov, alifatskih ketonov, estrov maščobnih kislin z alifatskimi alkoholi ali vode.
15. Postopek po enem ali več od zahtevkov 1 do 14, označen s tem, da pripravimo spojine s formulo IV po zahtevku 13 brez izoliranja spojin s formulo IV.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU3402/91A HU215840B (hu) | 1991-10-30 | 1991-10-30 | Eljárás 2-klór-tiazol-származékok előállítására |
| HU913404A HU207724B (en) | 1991-10-30 | 1991-10-30 | New process for producing thiazols |
| HU3403/91A HU215850B (hu) | 1991-10-30 | 1991-10-30 | Eljárás tiocianáto-keton-származékok előállítására |
| HU9201125A HUT66222A (en) | 1992-04-03 | 1992-04-03 | 2-hydroxy-4-methyl-5-halogenoalkyl-1,3-thiazole derivatives and process for producing them |
| HUP9201124A HU215849B (hu) | 1992-04-03 | 1992-04-03 | Eljárás 2-klór-4-metil-5-(halogén-alkil)-1,3-tiazol-származékok előállítására |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9200292A SI9200292A (en) | 1993-06-30 |
| SI9200292B true SI9200292B (sl) | 1999-06-30 |
Family
ID=27517525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9200292A SI9200292B (sl) | 1991-10-30 | 1992-10-30 | Nov postopek za pripravo 4-metil-5-(2-kloroetil)-tiazola in njegovih analogov |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5648498A (sl) |
| EP (2) | EP0619815B1 (sl) |
| JP (1) | JP3190959B2 (sl) |
| KR (1) | KR100218131B1 (sl) |
| AT (1) | ATE151761T1 (sl) |
| AU (1) | AU664868B2 (sl) |
| CA (1) | CA2121488A1 (sl) |
| CZ (1) | CZ283402B6 (sl) |
| DE (1) | DE69219154T2 (sl) |
| DK (1) | DK0619815T3 (sl) |
| ES (1) | ES2100365T3 (sl) |
| FI (1) | FI105476B (sl) |
| GR (1) | GR3023842T3 (sl) |
| HK (1) | HK93397A (sl) |
| HR (1) | HRP921128B1 (sl) |
| HU (1) | HU217079B (sl) |
| IL (1) | IL103586A (sl) |
| IS (1) | IS1688B (sl) |
| LV (1) | LV12130B (sl) |
| NO (1) | NO304650B1 (sl) |
| PL (1) | PL172013B1 (sl) |
| SI (1) | SI9200292B (sl) |
| SK (1) | SK279665B6 (sl) |
| WO (1) | WO1993009107A1 (sl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19548417A1 (de) * | 1995-12-22 | 1997-06-26 | Bayer Ag | Verfahren zur Herstellung von 2-Chlor-5-chlormethylthiazol |
| HUP0900267A2 (en) | 2009-04-30 | 2011-03-28 | Sanofi Aventis | Process for preparing of thiazole amines and intermediates thereof |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1808893A (en) * | 1931-06-09 | Leon c | ||
| GB456751A (en) * | 1935-05-13 | 1936-11-13 | Ig Farbenindustrie Ag | Process for the manufacture of 4-alkyl-5-hydroxy-alkylthiazoles |
| CH200248A (de) * | 1937-03-12 | 1938-09-30 | Hoffmann La Roche | Verfahren zur Darstellung von 4-Methyl-5-B-chloräthylthiazol. |
| US2395453A (en) * | 1944-02-26 | 1946-02-26 | Rohm & Haas | Beta-thiocyano ketones and method for their preparation |
| FR1274353A (fr) * | 1955-09-28 | 1961-10-27 | Procédé de préparation des méthyl-4 bêta-halogénoéthyl-5 thiazoles et de leurs sels | |
| DE1082903B (de) * | 1957-10-11 | 1960-06-09 | Basf Ag | Verfahren zur Herstellung von Rhodanverbindungen |
| DE1515197C3 (de) * | 1964-05-06 | 1974-08-15 | Steigerwald Strahltechnik Gmbh, 8000 Muenchen | Energiestrahl-Schweiß verfahren |
| BE668231A (sl) * | 1964-08-12 | |||
| US3670004A (en) * | 1969-01-07 | 1972-06-13 | Buckman Labor Inc | Thiocyano substituted acrylates and propionates and their use as pesticides |
| FR2152345A1 (en) * | 1971-09-06 | 1973-04-27 | Roussel Uclaf | Alpha-(2-thiazolyl)oxyalkanoic acids and derivatives - - with analgesic,antiinflammatory and antipyretic activity |
| DE2236796A1 (de) * | 1972-07-27 | 1974-02-07 | Georg Dipl Chem Dr Herbertz | 2-hydroxy-4-methyl-5-(2-chloraethyl)thiazol |
| DE2423981A1 (de) * | 1974-05-17 | 1975-11-27 | Bayer Ag | Alpha - halogenketone |
| DE2339109A1 (de) * | 1973-08-02 | 1975-02-20 | Bayer Ag | Alpha-halogenketone |
| DE2823658A1 (de) * | 1978-05-30 | 1979-12-06 | Bayer Ag | Mittel zur bekaempfung von pflanzenbakteriosen |
| US4377693A (en) * | 1979-10-01 | 1983-03-22 | Monsanto Company | 2-Chloro-4,5-disubstituted-thiazoles useful as herbicidal safeners |
| US4284426A (en) * | 1979-10-01 | 1981-08-18 | Monsanto Company | 2-Chloro-4,5-disubstituted-thiazoles useful as herbicidal safeners |
| US4284784A (en) * | 1980-05-22 | 1981-08-18 | Merck & Co., Inc. | Process for the preparation of 4-methyl thiazole |
| SU943233A1 (ru) * | 1980-07-18 | 1982-07-15 | Ереванский государственный университет | @ -Роданвинилметилкетон в качестве мономера дл синтеза ионитов и полиэлектролитов и способ его получени |
| GB8705447D0 (en) * | 1987-03-09 | 1987-04-15 | Autopia Terakat Accessories Lt | Glass frail |
| US4822813A (en) * | 1987-03-11 | 1989-04-18 | Uniroyal Chemical Ltd./Uniroyal Chemical Ltee | 3-(2-Haloalkyl)-1,4-oxathiins and 2-(2-haloalkyl)-1,4-dithiins, and treatment of leukemia and tumors therewith |
| SE8900564D0 (sv) * | 1989-02-17 | 1989-02-17 | Astra Ab | Novel medicinal use |
| US5180833A (en) * | 1990-03-16 | 1993-01-19 | Takeda Chemical Industries, Ltd. | Process for the preparation of chlorothiazole derivatives |
| HU206198B (en) * | 1990-09-21 | 1992-09-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing rhodanidoisobutyric acid |
-
1992
- 1992-10-29 HR HR1125/92A patent/HRP921128B1/xx not_active IP Right Cessation
- 1992-10-29 IL IL103586A patent/IL103586A/xx not_active IP Right Cessation
- 1992-10-29 IS IS3937A patent/IS1688B/is unknown
- 1992-10-30 US US08/232,207 patent/US5648498A/en not_active Expired - Lifetime
- 1992-10-30 JP JP50829893A patent/JP3190959B2/ja not_active Expired - Lifetime
- 1992-10-30 WO PCT/HU1992/000042 patent/WO1993009107A1/en active IP Right Grant
- 1992-10-30 AU AU29123/92A patent/AU664868B2/en not_active Ceased
- 1992-10-30 KR KR1019940701422A patent/KR100218131B1/ko not_active IP Right Cessation
- 1992-10-30 CZ CZ941034A patent/CZ283402B6/cs not_active IP Right Cessation
- 1992-10-30 AT AT92923097T patent/ATE151761T1/de not_active IP Right Cessation
- 1992-10-30 DK DK92923097.7T patent/DK0619815T3/da active
- 1992-10-30 ES ES92923097T patent/ES2100365T3/es not_active Expired - Lifetime
- 1992-10-30 SK SK501-94A patent/SK279665B6/sk unknown
- 1992-10-30 CA CA002121488A patent/CA2121488A1/en not_active Withdrawn
- 1992-10-30 PL PL92303342A patent/PL172013B1/pl unknown
- 1992-10-30 EP EP92923097A patent/EP0619815B1/en not_active Expired - Lifetime
- 1992-10-30 DE DE69219154T patent/DE69219154T2/de not_active Expired - Lifetime
- 1992-10-30 EP EP92118606A patent/EP0546306B1/en not_active Expired - Lifetime
- 1992-10-30 HU HU9401262A patent/HU217079B/hu not_active IP Right Cessation
- 1992-10-30 SI SI9200292A patent/SI9200292B/sl unknown
-
1994
- 1994-04-28 NO NO940004A patent/NO304650B1/no not_active IP Right Cessation
- 1994-04-29 FI FI941996A patent/FI105476B/fi active
-
1995
- 1995-06-05 US US08/464,308 patent/US5534644A/en not_active Expired - Lifetime
-
1997
- 1997-06-19 GR GR970401480T patent/GR3023842T3/el unknown
- 1997-06-26 HK HK93397A patent/HK93397A/xx not_active IP Right Cessation
-
1998
- 1998-04-16 LV LVP-98-68A patent/LV12130B/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Small et al. | Comparison of some properties of thiolsulfonates and thiolsulfinates | |
| US20180079725A1 (en) | Method for producing pyrazole derivative | |
| ES2376475T3 (es) | Procedimiento para la producción de un compuesto de aminometiltiazol. | |
| SI9200292B (sl) | Nov postopek za pripravo 4-metil-5-(2-kloroetil)-tiazola in njegovih analogov | |
| HU225458B1 (en) | Process for the preparation of thiazole derivatives, intermediates and preparation thereof | |
| US2864849A (en) | Thiophosphoric acid esters and their production | |
| SU1072800A3 (ru) | Способ получени гидрогалогенидов 2-меркаптоэтиламина и его вариант | |
| Piper et al. | Derivatives of 2-aminoethanethiol related to spermine and spermidine | |
| EP1467980B1 (de) | Verfahren zur herstellung von halogenierten 2-(3-butenylsulfanyl)-1, 3- thiazolen | |
| Furin et al. | Synthesis of Sulfur-containing Heterocyclic Compounds Based on Isothiocyanate Derivatives of Perfluoroolefins. | |
| US2829111A (en) | Azidoethyl-thiophosphoric acid esters | |
| GB921558A (en) | Thiophosphonic acid esters | |
| US2729668A (en) | Process for making diethoxyphosphoryl tetramethyldiamidothiophosphate | |
| US3035082A (en) | Disulfides of the phosphoric, phosphonic and phosphinic acid series and process for the production thereof | |
| DE2645748C2 (de) | Verfahren zur Herstellung von D,L-Cystein | |
| US2646440A (en) | Organic arseno polysulfides | |
| JPS6144867B2 (sl) | ||
| GB847550A (en) | Phosphonic acid esters | |
| US3491146A (en) | (arylthioureidoalkyl)tri-alkylammonium halides | |
| KR790001362B1 (ko) | 0,0-디알킬-s-벤질티오포스페이트의 제조방법 | |
| GB884206A (en) | 4-alkoxymetanilamides and compositions containing them | |
| DE1670921A1 (de) | Verfahren zur Herstellung von 3-Acylamino-1,2-benzisothiazolen | |
| YU95292A (sh) | Novi postupak za dobijanje 4-metil-5-(-2-hloro-etil)-tiazola i njegovih analoga | |
| CS215073B2 (en) | Method of making the derivatives of the 5-phenylselenobenzimidazole | |
| DE3225507A1 (de) | Fluorethoxyphenyl-(di)thiophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen |