CS195370B1 - Method of producing 2-phenylthiazol-4,5-dicarboxanhydride - Google Patents
Method of producing 2-phenylthiazol-4,5-dicarboxanhydride Download PDFInfo
- Publication number
- CS195370B1 CS195370B1 CS540278A CS540278A CS195370B1 CS 195370 B1 CS195370 B1 CS 195370B1 CS 540278 A CS540278 A CS 540278A CS 540278 A CS540278 A CS 540278A CS 195370 B1 CS195370 B1 CS 195370B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenylthiazole
- dimethoxyethane
- mol
- thionyl chloride
- dry
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- TVHXQIGBVCWCIS-UHFFFAOYSA-N 2-phenyl-1,3-thiazole-4,5-dicarboxylic acid Chemical compound S1C(C(O)=O)=C(C(=O)O)N=C1C1=CC=CC=C1 TVHXQIGBVCWCIS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- -1 2-phenylthiazole-4,5-dicarboxylic acid monosodium salt Chemical compound 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000000921 elemental analysis Methods 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 claims 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- FZWLAAWBMGSTSO-QDNHWIQGSA-N S1C=NC(=C1[2H])[2H] Chemical compound S1C=NC(=C1[2H])[2H] FZWLAAWBMGSTSO-QDNHWIQGSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález sa týká spósobu přípravy 2-fenyltiazol-4,5-dikarboxanhydridu vzorca
Podlá známého postupu sa táto zlúcenina připravuje pósobením chloridu tionylu na monodraselnú sol kyseliny 2-feny11iazo1-4,5-dikarboxylovej . Literatura, ktorá popisuje tuto syntézu, uvádza výtažky 53 %, t. t. 187,2 až 191,2 °C /rozmedzie teploty topenia’ poukazuje na znečistěný produkt/. Zistilo sa, že týmto postupom sa dá připravit produkt vo výtažku len 12 až 15 %· Uvedenu nevýhodu odstraňuje postup podlá vynálezu, ktorého podstatou je, že sa nechá reagovat monodraselná sol kyseliny 2-f eny J. t iazol-4,5-d ikarboxy love j s 20 Z raolárnym prebytkom chloridu tionylu v 1,2-dimetoxyetáne za přítomnosti pyridinu pri teplote 80 °C. Získá sa produkt vo výťaž-
Claims (1)
- PREDMET Spósob přípravy 2-fenyltiazol-4,5-dikarboxanhydridu pósobením chloridu tionylu na monodraselnú sol kyseliny 2-fenyltiazol-4,5-dikarboxylovej vyznačujúci sa tým, 2 ku 32 až 35 Z podstatné vyššej čistoty, ako podlá známej metody přípravy. Příklad Do zmesi 28,7 g /0,10 mol/ monodraselnej soli kyseliny 2-fenyltiazol-4,5-dikarboxylovej, 14,3 g /0,12 mol’/ chloridu tionylu a 150 ml suchého 1,2-dimetoxyetánu sa za miešania přidá v príebehu 20 min roztok 7,9 g /0,1 mol/ suchého pyridinu v 10 ml suchého 1,2-dimet0xyetánu tak, aby teplota ťeakčnej zmesi bola 80 °C. Potom sa zmes pri uvedenej teplote ešte 5 min mieša, za horúca sa odfiltruje, filtrát sa ochladí, vylúčené krystaly žltej farby sa odfíltrujú, premyjú éterom a vysušia. Kryštalizácia z dichlóretánu, svetložlté ihličky vo výtažku 32 až 35 Z teorie, t. t. 201 až 202 °C. IČ - spektrálné charakteristiky: pas/co/ 1789 cm-1j VS/CO/ 1853 cm-1. Okrem IČ - spektier bola zlúčenina charakterizovaná prvkovou elementárnou analýzou a - NMR spektrami. VYNÁLEZ *U že reakcia sa uskutočňuje v rozpúštadle 1 , 2-dimetoxyetáne, za přítomnosti, pyridinu s 20 Z molárnymi přebytku chloridu tionylu pri teplote varu rozpúštadla. Severoprafia, n. xívod 7, Moet 1 953 70
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS540278A CS195370B1 (en) | 1978-08-18 | 1978-08-18 | Method of producing 2-phenylthiazol-4,5-dicarboxanhydride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS540278A CS195370B1 (en) | 1978-08-18 | 1978-08-18 | Method of producing 2-phenylthiazol-4,5-dicarboxanhydride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195370B1 true CS195370B1 (en) | 1980-01-31 |
Family
ID=5398863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS540278A CS195370B1 (en) | 1978-08-18 | 1978-08-18 | Method of producing 2-phenylthiazol-4,5-dicarboxanhydride |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS195370B1 (cs) |
-
1978
- 1978-08-18 CS CS540278A patent/CS195370B1/cs unknown
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