Morpholine → Methyl 2-morpholinothiazole-4-carboxylate

HRID 1424339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424339
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C1COCC1.C(OCC)(=O)C>[O:14]1[CH2:15][CH2:16][N:11]([C:2]2[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=2)[CH2:12][CH2:13]1

Komponenten

5

Edukt 2

HCID 8083MorpholineHCID 2763213Methyl 2-bromothiazole-4-carboxylate

Produkt 1

HCID 86700889Methyl 2-morpholinothiazole-4-carboxylateAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of methyl 2-bromothiazole-4-carboxylate (0.20 g, 0.901 mmol) in THF (10 mL) was treated with morpholine (0.17 mL, 1.94 mmol) and refluxed for 18 h. The reaction was then diluted with ethyl acetate and washed with sat. NaHCO3 (1×), brine (1×) and dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (2.5×10 cm, 50% AcOEt/CH2Cl2) to give the title material (0.192 g, 92%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ ppm: 7.44 (s, 1H) 3.82 (s, 3H) 3.75 (m, 4H) 3.45 (m, 4H).

Aufarbeitung

  1. temperaturerefluxed for 18 h
  2. washwashed with sat. NaHCO3 (1×), brine (1×)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (2.5×10 cm, 50% AcOEt/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-9af68919aab545cf8c8d886551afd83e
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927688B2

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