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Triethylamine → [4-(3,5-Dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl)amine

HRID 1062626
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1062626
Br.Br[CH:3]([C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)[C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[CH:7]=1)=O.[NH2:20][C:21]([NH2:23])=[S:22].C(N(CC)CC)C>C(#N)C>[CH3:13][C:8]1[CH:7]=[C:6]([C:4]2[N:20]=[C:21]([NH2:23])[S:22][C:3]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:11]=[C:10]([CH3:12])[CH:9]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2723790ThioureaHCID 222823612-Bromo-1-(3,5-dimethylphenyl)-2-(4-pyridyl)ethanone hydrocbromide

Produkt 1

HCID 9925734[4-(3,5-Dimethylphenyl)-5-(4-pyridyl)-1,3-thiazol-2-yl)amineAusbeute 55,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-1-(3,5-dimethylphenyl)-2-(4-pyridyl)ethanone hydrobromide (5.0 g, 13 mmol) and thiourea (1.0 g, 14 mmol) in acetonitrile (60 mL) was added dropwise triethylamine (1.9 ml, 14 mmol) and the mixture was stirred at room temperature for 3 h. The solvent was concentrated under reduced pressure and a saturated aqueous sodium hydrogencarbonate solution was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with water and the solvent was evaporated. The obtained crude crystals were recrystallized from ethyl acetate to give the title compound (2.0 g, 7.2 mmol, yield 55%).

Aufarbeitung

  1. concentrationThe solvent was concentrated under reduced pressure
  2. additiona saturated aqueous sodium hydrogencarbonate solution was added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customthe solvent was evaporated
  6. customThe obtained crude crystals
  7. customwere recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0d55bbe93c7542db9b24d264ab5f7419
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06962933B1

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