Water → HCID 178504798, compound

To a suspension of 4-(methylsulfonyl)aniline (3.53 g, 20.2 mmol) in toluene (100 mL), trimethylaluminum (15.2 ml, 2M solution in toluene, 30.2 mmol) was added over 15 minutes. The reaction mixture was warmed to room temperature and stirred for 2.5 hours. A solution of 4-fluorobenzonitrile (5 g, 40.3 mmol) in toluene (100 mL) was added over 10 minutes and the reaction mixture heated to 80–85° C. After 20 hours, the reaction mixture was cooled to room temperature and poured over a slurry of silica gel in chloroform. After filtration, the residue was washed with a mixture of methylene chloride/methanol (2/1). The combined filtrates were concentrated in vacuo and the resulting yellowish solid stirred with a mixture of hexane/ether (2/1, 1000 mL). The intermediate was filtered and concentrated. The pale yellow solid 4-fluoro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (5.25 g, 87%) was used in the next reaction without further purification: mp (DSC) 206.2° C. Anal. Calc'd for C14H13N2FSO3.1.25 H2O: C, 53.41; H, 4.91; N, 8.90. Found: C, 53.08; H, 4.50; N, 8.61.

1. additionwas added over 15 minutes
2. temperaturethe reaction mixture heated to 80–85° C
3. waitAfter 20 hours
4. temperaturethe reaction mixture was cooled to room temperature
5. filtrationAfter filtration
6. washthe residue was washed with a mixture of methylene chloride/methanol (2/1)
7. concentrationThe combined filtrates were concentrated in vacuo
8. stirringthe resulting yellowish solid stirred with a mixture of hexane/ether (2/1, 1000 mL)
9. filtrationThe intermediate was filtered
10. concentrationconcentrated
11. customThe pale yellow solid 4-fluoro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (5.25 g, 87%) was used in the next reaction without further purification

ORD record

ord-bc61c6c3191f4d86909b9d9ddf356d0b

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07220770B2