Reaktion #711412

Reaktionsgleichung

2-Bromo-1-(4-nitrophenyl)ethanone

2-phenylethanethioamide

Water

hydrochloric acid

NH4OH

→

title compound

4-(2-benzylthiazol-4-yl)aniline

Lösungsmittel

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution was transferred to a 250 mL round bottom flask
2. 2
   Temperaturwas heated
3. 3
   Temperaturat reflux
4. 4
   workup.DISSOLUTIONwere dissolved
5. 5
   Temperaturthe mixture was heated
6. 6
   Temperaturat reflux for 2 hours
7. 7
   Temperaturto cool
8. 8
   FiltrationThe material was filtered through a pad of diatomaceous earth
9. 9
   Waschenthe pad was washed with 50 mL of ethyl acetate
10. 10
    WaschenThe filtrate was washed with 100 mL of water
11. 11
    Extraktionthe aqueous phase was extracted with an additional 50 mL of ethyl acetate
12. 12
    TrocknenThe combined organic fractions were dried over sodium sulfate
13. 13
    Filtrationfiltered
14. 14
    Sonstigethe solvent was removed under reduced pressure
15. 15
    workup.DISSOLUTIONThe material was re-dissolved in 50 mL of ethyl acetate
16. 16
    Filtrationfiltered through a ¼-inch pad of silica gel
17. 17
    WaschenThe pad was washed with an additional 50 mL of ethyl acetate
18. 18
    Einengenthe combined filtrate was concentrated

Vorschrift

2-Bromo-1-(4-nitrophenyl)ethanone (0.5 g, 2.049 mmol) and 2-phenylethanethioamide (0.310 g, 2.049 mmol) were combined in ethanol (10 ml) in a 20 mL microwave reaction vessel and heated at 140° C. for 15 minutes. The solution was transferred to a 250 mL round bottom flask where it immediately solidified. The material was diluted with an additional ethanol (10 ml) and was heated at reflux with stirring until the solids were dissolved. Water (5.0 ml, 278 mmol), and hydrochloric acid (1 ml, 12.00 mmol) were added. Iron (0.625 g, 11.19 mmol) was added and the mixture was heated at reflux for 2 hours. The mixture was allowed to cool and 5 mL NH4OH was added. The material was filtered through a pad of diatomaceous earth and the pad was washed with 50 mL of ethyl acetate. The filtrate was washed with 100 mL of water and the aqueous phase was extracted with an additional 50 mL of ethyl acetate. The combined organic fractions were dried over sodium sulfate, filtered, and the solvent was removed under reduced pressure. The material was re-dissolved in 50 mL of ethyl acetate and filtered through a ¼-inch pad of silica gel. The pad was washed with an additional 50 mL of ethyl acetate and the combined filtrate was concentrated to provide the title compound.

Quelle