p-Tolunitrile → HCID 178425632, compound

To a suspension of 4-(methylsulfonyl)aniline (3.57 g, 20.9 mmol) in toluene (150 mL), trimethylaluminum (15.6 ml, 2M solution in toluene, 31.4 mmol) was added over 15 minutes. The reaction mixture was warmed to room temperature and stirred for 2.5 hours. A solution of 4-methylbenzonitrile (5 ml, 41.8 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 are concentrated in vacuo and the resulting yellowish solid was stirred with a mixture of hexane/ether (2/1, 600 mL). The intermediate was filtered and washed with more of hexane/ether (2/1). The pale yellow solid 4-methyl-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (5.3 g, 88%) was used in the next reaction without further purification: mp (DSC) 213° C. Anal. Calc'd for C15H16N2SO2: C, 62.48; H, 5.59; N, 9.71. Found: C, 62.00, H, 5.52; N, 9.60.

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 are concentrated in vacuo
8. stirringthe resulting yellowish solid was stirred with a mixture of hexane/ether (2/1, 600 mL)
9. filtrationThe intermediate was filtered
10. washwashed with more of hexane/ether (2/1)
11. customThe pale yellow solid 4-methyl-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (5.3 g, 88%) was used in the next reaction without further purification

ORD record

ord-ce4b3b50e4fd4060b8085455a8e6f07b

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613789B2