Hydrochloric Acid → 4-(2-Benzylthiazol-4-yl)aniline

Temperature

140 °C

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.

1. customThe solution was transferred to a 250 mL round bottom flask
2. temperaturewas heated
3. temperatureat reflux
4. dissolutionwere dissolved
5. temperaturethe mixture was heated
6. temperatureat reflux for 2 hours
7. temperatureto cool
8. filtrationThe material was filtered through a pad of diatomaceous earth
9. washthe pad was washed with 50 mL of ethyl acetate
10. washThe filtrate was washed with 100 mL of water
11. extractionthe aqueous phase was extracted with an additional 50 mL of ethyl acetate
12. dry with materialThe combined organic fractions were dried over sodium sulfate
13. filtrationfiltered
14. customthe solvent was removed under reduced pressure
15. dissolutionThe material was re-dissolved in 50 mL of ethyl acetate
16. filtrationfiltered through a ¼-inch pad of silica gel
17. washThe pad was washed with an additional 50 mL of ethyl acetate
18. concentrationthe combined filtrate was concentrated

ORD record

ord-3f4ebb7ed1c14c9792b833efd0771e13

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09302989B2