Potassium Carbonate → 2-Chloro-4-(pyrrolidin-1-ylmethyl)-thiazole

HRID 1046430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1046430
[Cl:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7]Cl)[N:6]=1.[NH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:6]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 109208992-Chloro-4-(chloromethyl)-1,3-thiazole

Produkt 1

HCID 581140122-Chloro-4-(pyrrolidin-1-ylmethyl)-thiazoleAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Chloro-4-chloromethyl-thiazole (610 mg, 3.6 mmol), pyrrolidine (0.4 mL, 4.8 mmol), and potassium carbonate (1.05 g, 7.6 mmol) were stirred in DMF (6 mL) for 5 hours. After completion, the reaction mixture was partitioned between ethyl acetate and water. The aqueous phase was thrice extracted with ethyl acetate and the combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (0-5% [8:1 EtOH:NH4OH(aq)]/DCM). This resulted in 457 mg (63% yield) of the title compound as a white solid.

Aufarbeitung

  1. customAfter completion, the reaction mixture was partitioned between ethyl acetate and water
  2. extractionextracted with ethyl acetate
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-5% [8:1 EtOH:NH4OH(aq)]/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-9030a0a4809f4b0b9877e571f8108c47
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569302B2

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