Chloroacetaldehyde → N-(pyridin-2-yl)thiazol-2-amine

HRID 1355430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1355430
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([NH2:10])=[S:9].Cl[CH2:12][CH:13]=O.NC(N)=O>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][CH:12]=[CH:13][N:10]=1

Komponenten

5

Edukt 3

HCID 33ChloroacetaldehydeHCID 1176UreaHCID 14904911-(2-Pyridyl)-2-thiourea

Produkt 1

HCID 956683N-(pyridin-2-yl)thiazol-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a flask was added 2-pyridyl thiourea (5-1) (3.48 g, 22.7 mmol), 30 mL ethanol, and 50% by weight chloroacetaldehyde (14.4 mL, 113.5 mol). The flask was then heated to reflux. As the mixture was heated, the urea slowly dissolved in solution. After 3 hours, the ethanol was removed under reduced pressure. Saturated aqueous NaHCO3 was then added to the flask and a white precipitate formed after vigorous bubbling. The precipitate was filtered and washed with water. The white solid was then dried under vacuum overnight with P2O5 drying agent. 1H NMR (CDCl3): δ10.95 (bs, 1H), 8.37 (d, 1H, J=4.2 Hz), 7.61 (t, 1H, J=7.0 Hz), 7.49 (d, 1H, J=3.5 Hz), 6.94 (d, 1H, J=8.3 Hz), 6.88 (t, 1H, J=7.1 Hz), 6.85 (d, 1H, J=3.7 Hz).

Aufarbeitung

  1. temperatureThe flask was then heated to reflux
  2. temperatureAs the mixture was heated
  3. customthe ethanol was removed under reduced pressure
  4. additionSaturated aqueous NaHCO3 was then added to the flask
  5. customa white precipitate formed after vigorous bubbling
  6. filtrationThe precipitate was filtered
  7. washwashed with water
  8. dry with materialThe white solid was then dried under vacuum overnight with P2O5 drying agent

Quellen und Nachweise

ORD-Eintrag
ord-97250dfcf326451baa856f284265bb86
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586423B2

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