Chloroacetaldehyde → (4-Methoxy-phenyl)thiazol-2-yl-amine

HRID 1713653

Reaktionsgleichung

Reaktionsgleichung von HRID 1713653
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH2:12])=[S:11])=[CH:5][CH:4]=1.Cl[CH2:14][CH:15]=O>CCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[S:11][CH:14]=[CH:15][N:12]=2)=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 33ChloroacetaldehydeHCID 6675494-Thioureidoanisole

Produkt 1

HCID 956680(4-Methoxy-phenyl)thiazol-2-yl-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of (4-methoxy-phenyl)-thiourea (3.0 g, 16.5 mmol) and a 45% aqueous solution of chloroacetaldehyde (12 mL, 82.4 mmol, 5.0 equiv) in EtOH (23 mL) is heated to reflux for 1 h. The resulting dark orange solution is allowed to cool to RT and concentrated in vacuo. NaHCO3 is then added to the oily residue until CO2 evolution subsides and a beige precipitate forms. The product is collected by vacuum filtration, washed thoroughly with water (600 mL), and dried in vacuo. Title compound: ES-MS: 207.0 [M+H]+; single peak at tR=5.32 min (System 1); Rf=0.17 (CH2Cl2/MeOH, 95/5).

Aufarbeitung

  1. temperatureto reflux for 1 h
  2. concentrationconcentrated in vacuo
  3. additionNaHCO3 is then added to the oily residue until CO2 evolution subsides
  4. filtrationThe product is collected by vacuum filtration
  5. washwashed thoroughly with water (600 mL)
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-73cbf53bae11469aa911c9e263bd879e
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795288B2

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