N,N-Diethylaniline → P-Toluenesulfonamide

Diethylaniline (0.33 μL, 2.1 μmol, 1.1 equiv) was added in one portion to a stirred solution of the amine (1.0 mg, 1.9 μmol, 1 equiv) in THF (0.1 mL) at 0° C. under an argon atmosphere and the solution was stirred for 5 nin. p-Toluenesulfonyl chloride (0.73 mg, 3.8 mol, 2.0 equiv) was then added in one portion to the above solution at 0° C. The reaction mixture was stirred at 0° C. for 1 hr and then quenched with a 1:1 mixture of saturated aqueous sodium hydrogen carbonate solution and water (4 mL). The mixture was diluted with ethyl acetate (10 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (10 mL) and the combined organic layer was dried over sodium sulfate. Concentration in vacuo left a yellow oil, which was purified by flash column chromatography (60% ethyl acetate-hexanes) to give the 4-methylphenyl sulfonamide derivative (1.2 mg, 93%) as a white solid.

1. stirringThe reaction mixture was stirred at 0° C. for 1 hr
2. customquenched with a 1:1 mixture of saturated aqueous sodium hydrogen carbonate solution and water (4 mL)
3. additionThe mixture was diluted with ethyl acetate (10 mL)
4. customthe layers were separated
5. extractionThe aqueous layer was extracted with ethyl acetate (10 mL)
6. dry with materialthe combined organic layer was dried over sodium sulfate
7. concentrationConcentration in vacuo
8. waitleft a yellow oil, which
9. customwas purified by flash column chromatography (60% ethyl acetate-hexanes)

ORD record

ord-be129ccaf2584f51b4b1a24500c166d6

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06809099B2