N-bromobutanimide → Ethyl 5-amino-2-bromothiazole-4-carboxylate

HRID 512542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512542
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([C:14]1[N:15]=[CH:16][S:17][C:18]=1[NH2:19])=[O:13])[CH3:10]>C(#N)C.CCOC(C)=O>[NH2:19][C:18]1[S:17][C:16]([Br:1])=[N:15][C:14]=1[C:12]([O:11][CH2:9][CH3:10])=[O:13]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 12620181Ethyl 5-amino-1,3-thiazole-4-carboxylate

Produkt 1

HCID 59355801Ethyl 5-amino-2-bromothiazole-4-carboxylateAusbeute 58,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (0.54 g, 3.03 mmol) was added to a solution of 5-aminothiazole-4-carboxylic acid ethyl ester (0.44 g, 2.53 mmol) [prepared according to the procedure described by Golankiewicz et al. (Tetrahedron, 41 (24), 5989-5994 (1985))] in acetonitrile (10 mL), and the mixture was stirred for 30 min. The reaction mixture was diluted with EtOAc (50 mL) and washed with 5% K2CO3 aq. solution (25 mL) followed by brine (25mL). The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography eluted with 15% EtOAc in hexane to give 0.37 g (58% yield) of the titled compound.

Aufarbeitung

  1. customprepared
  2. washwashed with 5% K2CO3 aq. solution (25 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with 15% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-939b78f90ce94b139a36b81af49567f9
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102637B2

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