Phenol → HCID 59498502, compound

To a suspension of 1.0 g (6.20 mmol) of N-phenylmethacrylamide in 4 ml of toluene was added 1.30 g (6.24 mmol) of phosphorus pentachloride and stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in 5 ml of DMF and then cooled to 0° C. To a solution of 1.17 g (12.4 mmol) of phenol in 5 ml of DMF was added 546 mg (13.6 mmol) of sodium hydride (60% in oil) under ice cooling and stirred for 5 minutes. The mixture was added portionwise to the above-described DMF solution of the residue under ice cooling and stirred at room temperature for 1 hour. The reaction mixture was poured into water wad extracted with tert-butyl methyl ether (twice). The combined organic layer was washed sequentially with water and saturated NaCl, dried over anhydrous MgSO4, and then concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain 1.28 g of phenyl 2-methyl-N-phenyl-2-propenimidate.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionThe residue was dissolved in 5 ml of DMF
3. temperaturecooled to 0° C
4. stirringstirred for 5 minutes
5. stirringstirred at room temperature for 1 hour
6. extractionwad extracted with tert-butyl methyl ether (twice)
7. washThe combined organic layer was washed sequentially with water and saturated NaCl
8. dry with materialdried over anhydrous MgSO4
9. concentrationconcentrated
10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1)

ORD record

ord-e8f1d8b036bd4c14b0aab1b50cfa4d6f

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278473B2