3-Methyl-2-butanone → 4-isopropyl-N-(2-phenylethyl)-1,3-thiazole-2-amine

HRID 732165

Reaktionsgleichung

Reaktionsgleichung von HRID 732165
[CH3:1][CH:2]([CH3:6])[C:3](=O)[CH3:4].BrBr.C([O-])(=O)C.[Na+].[C:14]1([CH2:20][CH2:21][NH:22][C:23]([NH2:25])=[S:24])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])O.[Na+]>CO>[CH:2]([C:3]1[N:25]=[C:23]([NH:22][CH2:21][CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:24][CH:4]=1)([CH3:6])[CH3:1]

Komponenten

7

Edukt 5

HCID 112513-Methyl-2-butanoneHCID 24408Bromine2×HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 735845(2-Phenylethyl)thiourea

Produkt 1

HCID 231432554-isopropyl-N-(2-phenylethyl)-1,3-thiazole-2-amineAusbeute 51,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 3-methyl-2-butanone (0.86 g) in methanol (10 mL) was added bromine (1.60 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 (1.60 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 chromatography (ethyl acetate:hexane=1:9-2:1 in volume ratio) to give the title compound (1.26 g, yield 51%) as colorless crystals.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7620a1798ae04af1b931a2782f547095
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585880B2

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