Methanesulfonyl chloride → HCID 86590466, Verbindung

HRID 1062323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1062323
Br.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[N:7]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C(Cl)Cl>[CH3:11][O:10][C:8]([C:6]1[N:7]=[C:3]([NH:2][S:13]([CH3:12])(=[O:15])=[O:14])[S:4][CH:5]=1)=[O:9]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 22286972HCID 22286972, Verbindung

Produkt 1

HCID 86590466HCID 86590466, VerbindungAusbeute 45,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a well stirred solution of methyl 2-amino-thiazole-4-carboxylate hydrobromide (Justus Liebigs Ann. Chem. 1951, 571, 44, Heterocycles 1997, 45, 1299) (13 g, 51 mmol) and TEA (40 mL, 290 mmol) in DCM (130 mL) at rt was added methanesulfonyl chloride (11 mL, 140 mmol) dropwise. After stirring for 1 h, the reaction mixture was filtered and the filtrate concentrated. The residue was re-suspended in ethyl acetate, filtered and chromatographed on silica gel (ethyl acetate/ethanol, 97:3) to provide 2-methanesulfonylamino-thiazole-4-carboxylic acid methyl ester (5.5 g). MS (ESI−) for C6H8N2O4S2 m/z 234.9 (M−H)−.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. concentrationthe filtrate concentrated
  3. filtrationfiltered
  4. customchromatographed on silica gel (ethyl acetate/ethanol, 97:3)

Quellen und Nachweise

ORD-Eintrag
ord-d9e8d63942444e7d918adc41c41c1ce9
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960664B2

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