4-Methoxybenzenesulfonyl chloride → HCID 22997079, compound

Participants

Reaction Conditions

Reaction Steps

4-(aminooxy)pentanenitrile (1.3 mmol, 150 mg) and 4-methoxybenzenesulfonylchloride (1.3 mmol, 272 mg) were combined in anhydrous THF with diisopropylethylamine (1.4 mmol, 0.69 mL) and a few crystals of DMAP. The reaction was stirred at 50° C. for 15 hours. The reaction was diluted in diethyl ether, washed with 1N HCl, 1N NaOH and brine and dried over mangesium sulfate. NMR analysis revealed that the isolated crude was the double sulfonyl chloride addition product. The aqueous NaOH fraction was acidified to neutral pH, extracted into ethyl acetate and dried over magnesium sulfate. The solvent was removed under vacuum leaving a very clean 195 mg (52%) crude product. Rf=0.4 (0.1:1 hexanes/ethyl acetate); H1-NMR (CDCl3): δ 7.82 (2H,d), 7.01 (2H,d), 6.84 (1H,s), 4.17 (1H,m), 3.88 (3H,s), 2.42 (2H,m), 1.88 (2H,m), 1.23 (3H,d).

Provenance & Evidence