DK148096B - Fremgangsmaade til fremstilling af (2-aminothiazol-4-yl)-eddikesyre-hydrochlorid - Google Patents
Fremgangsmaade til fremstilling af (2-aminothiazol-4-yl)-eddikesyre-hydrochlorid Download PDFInfo
- Publication number
- DK148096B DK148096B DK065081AA DK65081A DK148096B DK 148096 B DK148096 B DK 148096B DK 065081A A DK065081A A DK 065081AA DK 65081 A DK65081 A DK 65081A DK 148096 B DK148096 B DK 148096B
- Authority
- DK
- Denmark
- Prior art keywords
- acetic acid
- aminothiazol
- acid hydrochloride
- preparing
- thiourea
- 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
- C07D277/32—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
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
148096
Den foreliggende opfindelse angår en fremgangsmåde til fremstilling af (2-aminothiazol-4-yl)-eddikesyre.
(2-Aminothiazol-4-yl)-eddikesyre og derivater deraf udgør sidekæder i semisyntetiske cephalosporiner. Fra J.Amer.Chem.
5 Soc., 1941, bd. 63, s. 2946-2948, er det kendt at fremstille 2-amino-4-alkylthiazoler ud fra estere af substituerede 2-aminothiazyl-4-eddikesyrer. Alkylaceteddikesyreester omsættes med brom til dannelse af bromalkylaceteddikeester, som omsættes med thiourinstof til dannelse af 2-aminothiazol-10 4-alkyleddikesyreesterhydrobromid. Denne fremgangsmåde er omstændelig og omfatter flere trin.
Det er formålet med opfindelsen at fremstille (2-aminothia-zol-4-yl)-eddikesyre-hydrochlorid på enkel måde. Dette opnås ifølge opfindelsen ved, at man til en suspension af thio-15 urinstof i vand ved temperaturer på 5-10°C sætter 4-chlor-acetoacetylchlorid, opløst i et chloreret carbonhydrid, og derpå afslutter reaktionen ved temperaturer på 25-30°C.
Ved fremgangsmåden ifølge opfindelsen fremstilles (2-amino-thiazol-4-yl)-eddikesyre-hydrochlorid direkte ud fra det 20 tilsvarende syrechlorid og thiourinstof, hvorimod man ved ovennævnte fremgangsmåde må anvende flere trin.
Som chloreret carbonhydrid anvendes carbontetrachlorid, chloroform, 1,2-dichlorethan, fortrinsvis methylenchlorid.
Ved en foretrukket udførelsesform for fremgangsmåden iføl-25 ge opfindelsen sættes det i det chlorerede opløsningsmiddel, fortrinsvis methylenchlorid, opløste 4-chloracetoacetyl-chlorid dråbevis til det i vand suspenderede thiourinstof i forhold til dets forbrug.
Derved holdes temperaturen på 1-30°C, fortrinsvis på 7-8°C.
30 Den mængde vand, der anvendes til fremstilling af thiourinstof suspensionen, er hensigtsmæssigt 125-250 g vand (pr. mol thiourinstof).
148096 2 4-Chloracetoacetylchlorid anvendes opløst i chlorerede carbonhydrider. Hensigtsmæssigt anvendes 3-30 mol opløsningsmiddel, fortrinsvis 8-25 mol opløsningsmiddel pr. mol 4-chloracetoacetylchlorid.
5 En foretrukket udførelsesform for fremgangsmåden ifølge opfindelsen består i, at man anvender et 4-chloracetoacetyl-chlorid, som er dannet ved chlorering af diketen i chlore-ret carbonhydrid, fortrinsvis methylenchlorid, ved temperaturer fra -10 til -25°C. Denne opløsning kan anvendes di-10 rekte.
Det ved fremgangsmåden ifølge opfindelsen fremstillede (2-aminothiazol-4-yl)-eddikesyre-hydrochlorid er stabilt og således lagerbestandigt såvel i opløsning som i fast form.
Fremgangsmåden ifølge opfindelsen illustreres nærmere i det 15 følgende eksempel.
Eksempel.
Til fremstilling af det anvendte udgangsmateriale, 4-chlor-acetoacetylChlorid, anbringes i en dobbeltkappekolbe 187,7 g methylenchlorid og 18,6 g diketen, og der afkøles til -25°C.
20 Til dette opløsningsmiddel ledes derpå chlor ved en temperatur på -20 til -25°C. Parallelt fremstilles i en rundkolbe en suspension af 15,2 g thiourinstof i 30,0 g vand, og denne suspension afkøles til 5°C. Til den til 5-7°C afkølede suspension af thiourinstof sættes dråbevis fra en 25 tildrypningstragt den ovenfor fremstillede 4-chloraceto-acetylchlorid-opløsning under kontinuerlig omrøring ved 7-8°C i løbet af 25 minutter, og efter endt tilsætning omrøres blandingen i yderligere 30 minutter ved 5-7°C, hvorefter svaleren fjernes, og omrøringen fortsættes i yderli-30 gere 60 minutter, hvorunder temperaturen stiger til 26-27°C. Derefter henstilles reaktionsblandingen i et køleskab til udfældning af (2-aminothiazol-4-yl)-eddikesyre-hydrochlorid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH128480 | 1980-02-18 | ||
| CH128480A CH642957A5 (de) | 1980-02-18 | 1980-02-18 | Verfahren zur herstellung von (2-aminothiazol-4-yl)-essigsaeure-hydrochlorid. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK65081A DK65081A (da) | 1981-08-19 |
| DK148096B true DK148096B (da) | 1985-03-04 |
| DK148096C DK148096C (da) | 1985-08-12 |
Family
ID=4206825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK65081A DK148096C (da) | 1980-02-18 | 1981-02-13 | Fremgangsmaade til fremstilling af (2-aminothiazol-4-yl)-eddikesyre-hydrochlorid |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4391979A (da) |
| EP (1) | EP0034340B1 (da) |
| JP (1) | JPS5914464B2 (da) |
| AR (1) | AR227302A1 (da) |
| AT (1) | ATE5774T1 (da) |
| AU (1) | AU537839B2 (da) |
| BG (1) | BG35187A3 (da) |
| BR (1) | BR8100912A (da) |
| CA (1) | CA1159456A (da) |
| CH (1) | CH642957A5 (da) |
| CS (1) | CS223891B2 (da) |
| DD (1) | DD156910A5 (da) |
| DE (1) | DE3161815D1 (da) |
| DK (1) | DK148096C (da) |
| ES (1) | ES8200882A1 (da) |
| FI (1) | FI810016L (da) |
| HU (1) | HU180624B (da) |
| IE (1) | IE50951B1 (da) |
| IL (1) | IL61954A (da) |
| IN (1) | IN153071B (da) |
| NO (1) | NO810532L (da) |
| PL (1) | PL126906B1 (da) |
| PT (1) | PT72517B (da) |
| RO (1) | RO80211A (da) |
| SU (1) | SU1015825A3 (da) |
| YU (1) | YU38381A (da) |
| ZA (1) | ZA81475B (da) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU542287B2 (en) * | 1982-06-17 | 1985-02-14 | Toyama Chemical Co. Ltd. | Process for producing 2-(2-aminothiazol-4-yl) glyoxylic acid derivative, it:s salt and intermediates therefor |
| EP0115770B2 (en) * | 1983-01-07 | 1996-06-19 | Takeda Chemical Industries, Ltd. | Thiazole Derivatives |
| US5145675A (en) * | 1986-03-31 | 1992-09-08 | Advanced Polymer Systems, Inc. | Two step method for preparation of controlled release formulations |
| CN101948446B (zh) * | 2010-08-30 | 2013-05-15 | 江苏华旭药业有限公司 | 一种2-氨基噻唑-4-基乙酸盐酸盐的制造方法 |
| CN102827099A (zh) * | 2012-08-20 | 2012-12-19 | 哈尔滨恒运科技开发有限公司 | 一种氨基噻唑乙酸盐酸盐的合成方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB558956A (en) * | 1942-04-24 | 1944-01-31 | Boots Pure Drug Co Ltd | Improvements relating to the manufacture of 2-aminothiazole |
| GB593024A (en) * | 1944-05-18 | 1947-10-07 | Kodak Ltd | Production of ª‰-2-thienoylpropionic acids and derivatives thereof |
| BE790569A (fr) * | 1971-10-27 | 1973-04-26 | Syntex Corp | Agents cardiovasculaires a base de thiazoles |
| FR2408613A2 (fr) | 1977-07-19 | 1979-06-08 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| DE2760484C2 (da) | 1976-04-14 | 1992-12-03 | Takeda Chemical Industries, Ltd., Osaka, Jp | |
| GB1555007A (en) * | 1976-05-25 | 1979-11-07 | Fujisawa Pharmaceutical Co | Intermediates in the preparation of substituted cepham carboxylic acid derivatives and the preparation thereof |
| FR2384781A2 (fr) | 1977-01-21 | 1978-10-20 | Roussel Uclaf | Nouvelles oximes derivees de l'article 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| FR2381053A1 (fr) | 1977-02-18 | 1978-09-15 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-thiadiazolyl thiomethyl 7-aminothiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| FR2384779A1 (fr) | 1977-03-25 | 1978-10-20 | Roussel Uclaf | Nouvelles oximes derivees de l'acide 3-chloro ou 3-methoxy 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| SE439312B (sv) | 1977-03-25 | 1985-06-10 | Roussel Uclaf | Sett att framstella nya oximderivat av 3-acetoximetyl-7-aminotiazolylacetamido cefalosporansyra |
| FR2390442A1 (fr) | 1977-05-13 | 1978-12-08 | Roussel Uclaf | Nouveaux produits derives de l'acide 2-(2-amino 4-thiazolyl) acetique et leur procede de preparation |
| US4308391A (en) * | 1979-10-01 | 1981-12-29 | Monsanto Company | 2-Amino-4-substituted-thiazolecarboxylic acids and their derivatives |
-
1980
- 1980-02-18 CH CH128480A patent/CH642957A5/de not_active IP Right Cessation
-
1981
- 1981-01-06 FI FI810016A patent/FI810016L/fi not_active Application Discontinuation
- 1981-01-09 ES ES498396A patent/ES8200882A1/es not_active Expired
- 1981-01-14 IE IE59/81A patent/IE50951B1/en unknown
- 1981-01-20 IN IN59/CAL/81A patent/IN153071B/en unknown
- 1981-01-21 IL IL61954A patent/IL61954A/xx unknown
- 1981-01-22 US US06/227,489 patent/US4391979A/en not_active Expired - Fee Related
- 1981-01-23 ZA ZA00810475A patent/ZA81475B/xx unknown
- 1981-02-04 CA CA000370031A patent/CA1159456A/en not_active Expired
- 1981-02-12 DE DE8181100996T patent/DE3161815D1/de not_active Expired
- 1981-02-12 AT AT81100996T patent/ATE5774T1/de not_active IP Right Cessation
- 1981-02-12 EP EP81100996A patent/EP0034340B1/de not_active Expired
- 1981-02-12 PL PL1981229648A patent/PL126906B1/pl unknown
- 1981-02-13 DK DK65081A patent/DK148096C/da not_active IP Right Cessation
- 1981-02-16 RO RO81103431A patent/RO80211A/ro unknown
- 1981-02-16 CS CS811099A patent/CS223891B2/cs unknown
- 1981-02-16 AR AR284307A patent/AR227302A1/es active
- 1981-02-16 BG BG050854A patent/BG35187A3/xx unknown
- 1981-02-16 YU YU00383/81A patent/YU38381A/xx unknown
- 1981-02-16 BR BR8100912A patent/BR8100912A/pt unknown
- 1981-02-16 HU HU8181372A patent/HU180624B/hu unknown
- 1981-02-16 DD DD81227653A patent/DD156910A5/de unknown
- 1981-02-17 NO NO810532A patent/NO810532L/no unknown
- 1981-02-17 SU SU813248457A patent/SU1015825A3/ru active
- 1981-02-17 JP JP56022165A patent/JPS5914464B2/ja not_active Expired
- 1981-02-17 AU AU67382/81A patent/AU537839B2/en not_active Ceased
- 1981-02-17 PT PT72517A patent/PT72517B/pt unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4769493A (en) | Process for producing tetrafluorophthalic acid | |
| DK148096B (da) | Fremgangsmaade til fremstilling af (2-aminothiazol-4-yl)-eddikesyre-hydrochlorid | |
| RU2378261C2 (ru) | Способ получения солевого соединения (4,5-дигидроизоксазол-3-ил)тиокарбоксамидина | |
| WO1998032747A1 (en) | Process for the preparation of thiazole derivatives | |
| NO772257L (no) | Fremgangsm}te for fremstilling av 2-lavere-alkyl-7-substituert-2- eller -3-cefem-4-karboksylsyrer | |
| DE69902071T2 (de) | Verfahren zur Herstellung von 2-substituierten Pyridinen | |
| US7825144B2 (en) | Method for the production of oxazoles by condensing aromatic aldehydes with α-ketoximes to N-oxides and then reacting the same with activated acid derivatives | |
| US4581466A (en) | Process for the preparation of benzo-fused, tetrachlorinated heterocyclic compounds | |
| EP0259663B1 (en) | Process for producing tetrafluorophihalic acid | |
| US4083866A (en) | Sulfonylamidino aminobenzaldehyde compounds | |
| RU2027704C1 (ru) | Способ получения 6-фтор-1,2-бензизотиазолов, ортозамещенное фенациловое производное и способ его получения | |
| DK163816B (da) | 1,4-dihalogenbutan-2,3-dioner til brug som mellemprodukter ved fremstillingen af 2-(2-aminothiazol-4-yl)glyoxylsyrederivater eller salte heraf og fremgangsmaade til fremstilling af mellemprodukterne | |
| SU607548A3 (ru) | Способ получени производных формамидина | |
| US4764621A (en) | Preparation of 2-chlorobenzthiazole | |
| CA1202624A (en) | Process for the preparation of tertiary alkyl cyanides | |
| KR810000816B1 (ko) | 4-벤조일피라졸 유도체 및 그의 알루미늄염의 제법 | |
| US4171442A (en) | Process for the preparation of 2,4,5-trichloropyrimidine | |
| US3940390A (en) | Process for the production of 2,3,4,5,6,7-hexahydrocyclopenta-(3)-1,3-oxazine-2,4-dione compounds | |
| US20080039663A1 (en) | Method For Producing 3-Halophthalic Acid Dichlorides | |
| US5298606A (en) | Process for the preparation of substituted azoxycyanides | |
| US4180510A (en) | Method for preparing thienylacetic acids | |
| SU808500A1 (ru) | Способ получени бис-(2,4-ди-МЕРКАпТО-6-ТРиАзиНил) диСульфидА | |
| US4125723A (en) | Process for the preparation of tetrachloropyrimidine | |
| SU437281A1 (ru) | Способ получени производных 2-(5нитро-2-фурил)-тиено/3,2- /пиримидина | |
| US3642776A (en) | 1-formyl-2-halogeno-azacycloalkenes and process for their production |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |