Methacrolein → 2-[4-(2-Furyl)phenyl]4-methyl-1-(4-sulfamoylphenyl)-1H-pyrrole

To a suspension of a α-4-sulfamoylanilino-α-[4-(2-furyl)phenyl]acetnitrile (0.28 g, 0.79 mmol) in anhydrous THF (3 mL) at −70° C. was added methacrolein (0.061 g, 0.87 mmol), and then dropwise lithium bis(trimethylsilyl)amide (0.83 mL, 1.0 M solution in hexane, 0.83 mmol). The reaction mixture was stirred at −60° C. to −65° C. for 1 hour, and then the temperature of the reaction mixture was allowed to return to room temperature, and the mixture was stirred for a further 2 hours. The reaction mixture was added a saturated aqueous solution of NH4Cl (10 mL) and the whole was extracted with ethyl acetate (10 mL×2). The organic layer was washed with water, dried over Na2SO4, and concentrated in vacuo. The residue was redissolved in toluene (5 mL) and heated at reflux temperature for 1 hour. The reaction mixture was concentrated in vacuo. The residue was purified by thin-layer chromatography eluting with hexane/ethyl acetate (2/1). The resulting solid was recrystallized from CH2Cl2—hexane to give the, title compound (0.012 g, 5.6% yield).

1. customto return to room temperature
2. stirringthe mixture was stirred for a further 2 hours
3. extractionthe whole was extracted with ethyl acetate (10 mL×2)
4. washThe organic layer was washed with water
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was redissolved in toluene (5 mL)
8. temperatureheated
9. temperatureat reflux temperature for 1 hour
10. concentrationThe reaction mixture was concentrated in vacuo
11. customThe residue was purified by thin-layer chromatography
12. washeluting with hexane/ethyl acetate (2/1)
13. customThe resulting solid was recrystallized from CH2Cl2—hexane

ORD record

ord-ca72466bf8d946fe90c15379f22b0c19

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949536B2