Water → Methyl 2-methoxy-5-phenylthiazole-4-carboxylate

HRID 1154754

Reaktionsgleichung

Reaktionsgleichung von HRID 1154754
Cl[C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.[CH3:17][O-:18].[Na+].O>CO>[CH3:17][O:18][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 12821997Methyl 2-chloro-5-phenyl-4-thiazolecarboxylate

Produkt 1

HCID 12821998Methyl 2-methoxy-5-phenylthiazole-4-carboxylateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Under a static N2 atm, a stirred solution of the compound of Example 2 (8.14 g, 32 mol) in 100 ml of methanol was treated dropwise with 7.6 g of 25% sodium methoxide in methanol. After stirring at ambient temperature for 24 hr, the mixture was added to H2O and extracted twice with ether. The ether layer was washed with H2O, dried over MgSO4 and concentrated in vacuo to yield a white solid which was recrystallized from methylcyclohexane to yield 5.5 g of methyl 2-methoxy-5-phenyl-4-thiazolecarboxylate as a white solid, m.p. 86°-88° C., yield 70%.

Aufarbeitung

  1. extractionextracted twice with ether
  2. washThe ether layer was washed with H2O
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto yield a white solid which
  6. customwas recrystallized from methylcyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-5f6a3c5eff844e1baa0a0ffcf4eb85ae
Quelldatensatz
uspto-grants-1981_11
Patentnummer
US04298375

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