Ethanol → N-(2-phenylethyl)-4-(pyridin-2-yl)-1,3-thiazol-2-amine

HRID 732171

Reaktionsgleichung

Reaktionsgleichung von HRID 732171
Br.Br[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=O.[C:12]1([CH2:18][CH2:19][NH:20][C:21]([NH2:23])=[S:22])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(=O)C.[Na+].C(O)C>O>[C:12]1([CH2:18][CH2:19][NH:20][C:21]2[S:22][CH:3]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=3)[N:23]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 735845(2-Phenylethyl)thioureaHCID 27762312-Bromo-1-(2-pyridinyl)-1-ethanone hydrobromide

Produkt 1

HCID 973106N-(2-phenylethyl)-4-(pyridin-2-yl)-1,3-thiazol-2-amineAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 2-bromo-1-pyridin-2-ylethanone hydrobromide (4.00 g), N-(2-phenylethyl)thiourea (3.60 g), sodium acetate (1.60 g) and ethanol (30 mL) was stirred with heating under reflux for 1 hr. After cooling, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and 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 (2.71 g, yield 48%) as a yellow oil.

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. 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-0ab8515fa9534e92a621e505e97bfcb0
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585880B2

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