Sulfuric Acid → 4-(6-Carboxyhexyl)-thiazole-5-carboxylic acid

HRID 972232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 972232
C[O:2][C:3]([C:5]1[S:9][CH:8]=[N:7][C:6]=1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[O:4].[OH-].[Na+].S(=O)(=O)(O)O>C(O)C>[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:6]1[N:7]=[CH:8][S:9][C:5]=1[C:3]([OH:4])=[O:2])([OH:18])=[O:17]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 538158814-(6-Carbomethoxy hexyl)-thiazole-5-carboxylic acid methylester

Produkt 1

HCID 214064084-(6-Carboxyhexyl)-thiazole-5-carboxylic acidAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To the solution of 16 g of crude 4-(6carbomethoxyhexyl)-thiazole-5-carboxylic acid methylester (VIII, R1 = H) in 50 ml of ethanol 100 ml of 2 N sodium hydroxide solution was added, the reaction mixture was refluxed for 30 minutes, then acidified with 5 N sulphuric acid under ice-cooling. On extracting the aqueous reaction mixture with 3 × 150 of ml ethyl acetate, the extract was dried over sodium sulphate and evaporated in vacuo. Recrystallization of the obtained crude product from diethylether afforded 9.4 g of 4-(6-carboxyhexyl)-thiazole-5carboxylic acid (IX, R1 = H). M.p.: 151°-153° C.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 30 minutes
  2. temperaturecooling
  3. extractionOn extracting the aqueous reaction mixture with 3 × 150 of ml ethyl acetate
  4. dry with materialthe extract was dried over sodium sulphate
  5. customevaporated in vacuo
  6. customRecrystallization of the
  7. customobtained crude product from diethylether

Quellen und Nachweise

ORD-Eintrag
ord-97738225ff26475295f1cca2de6157e9
Quelldatensatz
uspto-grants-1977_10
Patentnummer
US04052407

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