Bromomethyl 4-methoxyphenyl ketone → 4-(4-Methoxy-phenyl)-2-methyl-thiazole

HRID 538588

Reaktionsgleichung

Reaktionsgleichung von HRID 538588
[C:1]([NH2:4])(=[S:3])[CH3:2].Br[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=O>O>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[N:4]=[C:1]([CH3:2])[S:3][CH:6]=2)=[CH:10][CH:11]=1

Komponenten

4

Edukt 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 2723949Thioacetamide

Produkt 1

HCID 7687654-(4-Methoxy-phenyl)-2-methyl-thiazoleAusbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of thioacetamide (16.0 g, 213 mmol) and 2-Bromo-1-(4-methoxy-phenyl)-ethanone (4.0 g, 17.5 mmol) was heated at 140° C. for 24 h under nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), water (25 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica gel (230-400 M, 1% EtOAc-Hexane) to get the desired product (2.5 g, 69%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organics was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified over silica gel (230-400 M, 1% EtOAc-Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2ef870e9d8da4304b4c6c51d49c74041
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865736B2

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