Bromine → 4-isobutyl-N-(2-phenylethyl)-1,3-thiazole-2-amine

HRID 732166

Reaktionsgleichung

Reaktionsgleichung von HRID 732166
BrBr.[C:3]([O-])(=O)[CH3:4].[Na+].[C:8]1([CH2:14][CH2:15][NH:16][C:17]([NH2:19])=[S:18])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])O.[Na+]>CO.CC(C)CC(=O)C>[CH2:9]([C:3]1[N:19]=[C:17]([NH:16][CH2:15][CH2:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:18][CH:4]=1)[CH:8]([CH3:14])[CH3:13]

Komponenten

7

Edukt 4

HCID 24408Bromine2×HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 735845(2-Phenylethyl)thiourea

Produkt 1

HCID 231432624-isobutyl-N-(2-phenylethyl)-1,3-thiazole-2-amineAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 7909Methyl Isobutyl KetoneLösungsmittel

Versuchsvorschrift

To a solution of 4-methyl-2-pentanone (2.00 g) in methanol (10 mL) was added bromine (3.20 g) at −30° C. The mixture was allowed to warm to room temperature and stirred until the red color of bromine disappeared. To the obtained colorless solution were added sodium acetate (3.20 g) and N-(2-phenylethyl)thiourea (1.80 g) and the mixture was stirred with heating under reflux for 4 hr. A saturated aqueous sodium hydrogencarbonate solution (10 mL) was added to the reaction mixture and the mixture was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio) to give the title compound (1.15 g, yield 41%) as pale-yellow crystals.

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 4 hr
  3. concentrationthe mixture was concentrated
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio)

Quellen und Nachweise

ORD-Eintrag
ord-6ac9e21dc8fa42be8e4cdf3dee343666
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585880B2

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