反应详情

温度

60 °C

To a solution of ethyl[(2-mercapto-4,5-dihydronaphtho[1,2-d]thiazol-6-yl)oxy]acetate (1.10 g, 3.42 mmol) in N,N-dimethylformamide (20 mL) were added diphenylmethane bromide (0.93 g, 3.76 mmol) and potassium carbonate (0.52 g, 3.76 mmol), and the mixture was stirred at 60° C. for 3 hours. This reaction mixture was diluted with ethyl acetate and water and, after phase separation, the aqueous layer was extracted with ethyl acetate. The pooled organic solution was washed with water, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in acetic acid (20 mL). To this solution was added concentrated sulfuric acid (10 ml), and the mixture was refluxed for 1 hour. After cooling, the reaction mixture was diluted with water and extracted with 2 portions of ethyl acetate. The pooled extract was washed with water, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure and the residue was crystallized from hexane-ethyl acetate to provide 0.58 g of the title compound. Yield 37%.

1. customafter phase separation
2. extractionthe aqueous layer was extracted with ethyl acetate
3. washThe pooled organic solution was washed with water
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under reduced pressure
7. dissolutionthe residue was dissolved in acetic acid (20 mL)
8. additionTo this solution was added concentrated sulfuric acid (10 ml)
9. temperaturethe mixture was refluxed for 1 hour
10. temperatureAfter cooling
11. additionthe reaction mixture was diluted with water
12. extractionextracted with 2 portions of ethyl acetate
13. extractionThe pooled extract
14. washwas washed with water
15. dry with materialdried over MgSO4
16. filtrationfiltered
17. concentrationThe filtrate was concentrated under reduced pressure
18. customthe residue was crystallized from hexane-ethyl acetate