Water → 4-Methyl-2-phenoxy-thiazole-5-carboxylic acid ethyl ester

HRID 1173039

Reaktionsgleichung

Reaktionsgleichung von HRID 1173039
Cl[C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[CH3:7][C:5]1[N:6]=[C:2]([O:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:3][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 996PhenolHCID 11430Potassium Carbonate2×HCID 594903Ethyl 2-chloro-4-methyl-1,3-thiazole-5-carboxylate

Produkt 1

HCID 576654844-Methyl-2-phenoxy-thiazole-5-carboxylic acid ethyl esterAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a solution of ethyl 2-chloro-4-methyl-1,3-thiazole-5-carboxylate (X-1) (0.25 g, 1.22 mmol) and phenol (0.15 g, 1.61 mmol) in acetone (3 mL) was added K2CO3 (0.25 g, 1.81 mmol). The mixture was heated for 18 h at 65° C. Additional K2CO3 (0.25 g) was added and the mixture was continued to heat at 70° C. for 24 h. Upon cooling, water was added (10 mL). The mixture was extracted with Et2O. The combined organics were dried with MgSO4 and concentrated. The crude material was purified by chromatography (EtOAc/hexanes) to give the title compound as a white solid (0.18 g, 56%). 1H NMR (CDCl3) δ 7.44 (m, 2H), 7.33-7.27 (m, 3H), 4.26 (q, J=7.1 Hz, 2H), 2.60 (s, 3H), 1.31 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. temperatureto heat at 70° C. for 24 h
  2. temperatureUpon cooling
  3. extractionThe mixture was extracted with Et2O
  4. dry with materialThe combined organics were dried with MgSO4
  5. concentrationconcentrated
  6. customThe crude material was purified by chromatography (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1ab957b567864ee187c01177daca1b3e
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834013B2

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