N-bromobutanimide → Ethyl 2-(bromomethyl)thiazole-5-carboxylate

HRID 1268892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1268892
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[S:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:14]=1>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:9][C:10]1[S:11][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][N:14]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 12808791Ethyl 2-methyl-1,3-thiazole-5-carboxylate

Produkt 1

HCID 21840919Ethyl 2-(bromomethyl)thiazole-5-carboxylateAusbeute 41,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (0.91 g, 5.1 mmol) was added to a solution of ethyl 2-methyl-thiazole-5-carboxylate (0.8 g, 4.7 mmol) in carbon tetrachloride. The resultant reaction mixture was stirred for one hour whilist being illuminated by a photoflood lamp. After removing the solvent from the reaction mixture the resultant material was partitioned between ethyl acetate and water. The organic phase was then separated off, dried (MgSO4) and the evaporated. Chromatography on silica, eluting with 30% ethyl acetate in hexane, gave ethyl 2-(bromomethyl)-1,3-thiazole-5-carboxylate (490 mgs), NMR: δH (300 MHz, DMSO-d6, 1.20–1.38 (3 H,t); 4.20–4.37 (2 H,q); 5.05 (2 H, s); 8.55 (1 H, s).

Aufarbeitung

  1. customThe resultant reaction mixture
  2. customwhilist being illuminated by a photoflood lamp
  3. customAfter removing the solvent from the reaction mixture the resultant material
  4. customwas partitioned between ethyl acetate and water
  5. customThe organic phase was then separated off
  6. dry with materialdried (MgSO4)
  7. washChromatography on silica, eluting with 30% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4daf22f70f514f42823ad518173ab37b
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199140B2

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