Pyrazole → HCID 56991616, compound

Temperature

100 °C

4-(1-Pyrazolyl)methylphenol [this was obtained in the following manner: A mixture of pyrazole (351 mg), 4-acetoxybenzyl bromide (1 g), anhydrous potassium carbonate (1.30 g) and anhydrous N,N-dimethylformamide (30 ml) was heated at 100° C. under stirring for 3 hours. The reaction mixture was then poured into ice-cooled saturated aqueous ammonium chloride solution (200 ml), which was extracted twice with ethyl acetate (50 ml). The organic layers were combined, washed with saturated sodium chloride solution (50 ml), dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in ethanol (20 ml), to which 5N aqueous sodium hydroxide solution (1.03 ml) was added, and the mixture was stirred at room temperature overnight. Then, water (10 ml) was added to the reaction mixture, which was concentrated under reduced pressure to remove most of the ethanol. The residue was poured into an ice-cooled mixture of acetic acid (310 mg) and water (100 ml), which was extracted twice with ethyl acetate (50 ml). The organic layers were combined, washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure.]was dissolved in anhydrous N,N-dimethylformamide (20 ml), to which 2-chloroethylcarbamic acid methyl ester (710 mg) and potassium carbonate (1.43 g) were added, and the mixture was heated at 60° C. under stirring for 6 hours. The reaction mixture was then poured into ice-cooled saturated aqueous ammonium chloride solution (100 ml), which was extracted twice with ethyl acetate (50 ml). The organic layers were combined, washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 128 mg of 2-[4-(1-pyrazolyl)methylphenoxy]ethylcarbamic acid methyl ester (compound 3). Yield, 10% (based upon 4-acetoxybenzyl bromide).

1. additionThe reaction mixture was then poured into ice-
2. extractionwas extracted twice with ethyl acetate (50 ml)
3. washwashed with saturated sodium chloride solution (50 ml)
4. dry with materialdried with anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in ethanol (20 ml), to which 5N aqueous sodium hydroxide solution (1.03 ml)
7. additionwas added
8. stirringthe mixture was stirred at room temperature overnight
9. additionThen, water (10 ml) was added to the reaction mixture, which
10. concentrationwas concentrated under reduced pressure
11. customto remove most of the ethanol
12. additionThe residue was poured into an ice-
13. temperaturecooled
14. additionmixture of acetic acid (310 mg) and water (100 ml), which
15. extractionwas extracted twice with ethyl acetate (50 ml)
16. washwashed with saturated sodium chloride solution
17. dry with materialdried with anhydrous magnesium sulfate
18. concentrationconcentrated under reduced pressure
19. dissolution]was dissolved in anhydrous N,N-dimethylformamide (20 ml), to which 2-chloroethylcarbamic acid methyl ester (710 mg) and potassium carbonate (1.43 g)
20. additionwere added
21. temperaturethe mixture was heated at 60° C.
22. stirringunder stirring for 6 hours
23. additionThe reaction mixture was then poured into ice-
24. temperaturecooled saturated aqueous ammonium chloride solution (100 ml), which
25. extractionwas extracted twice with ethyl acetate (50 ml)
26. washwashed with saturated sodium chloride solution
27. dry with materialdried with anhydrous magnesium sulfate
28. concentrationconcentrated under reduced pressure

ORD record

ord-28107a19a6e04cf6aed1e6d97c7eabcd

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05684022