2-Amino-5-methylthiazole → Ethyl 2,6-dimethylimidazo[2,1-b]thiazole-5-carboxylate

HRID 560290Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 560290
[CH3:1][C:2]1[S:6][C:5]([NH2:7])=[N:4][CH:3]=1.[CH2:8]([O:10][C:11](=[O:17])[CH:12](Br)[C:13](=O)[CH3:14])[CH3:9]>CC(C)=O>[CH2:8]([O:10][C:11]([C:12]1[N:4]2[C:5]([S:6][C:2]([CH3:1])=[CH:3]2)=[N:7][C:13]=1[CH3:14])=[O:17])[CH3:9]

Komponenten

4

Edukt 2

HCID 3517702-Amino-5-methylthiazoleHCID 11206579Ethyl 2-bromo-3-oxobutanoate

Produkt 1

HCID 15026034Ethyl 2,6-dimethylimidazo[2,1-b]thiazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 5-methyl-2-aminothiazole (7.09 mmol) and 2-bromo-3-oxo-butyric acid ethyl ester (8.51 mmol) in acetone (17 mL) is stirred for 16 h at RT and for additional 7 h at reflux. The solvents are removed in vacuo, chloroform and sat aq. NaHCO3 solution are added, the layers are separated and the aq. layer is extracted with chloroform. The combined organic layers are dried over MgSO4 and concentrated in vacuo to give a crude product which is purified by FC (heptane to heptane/EtOAc 6/4). LC-MS: tR=0.80 min; [M+H]+=225.3.

Aufarbeitung

  1. temperatureat reflux
  2. customThe solvents are removed in vacuo, chloroform
  3. additionare added
  4. customthe layers are separated
  5. extractionthe aq. layer is extracted with chloroform
  6. dry with materialThe combined organic layers are dried over MgSO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-94e798d7b7f048bd93d3d1b9dae2b6e4
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063099B2

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