N-tert-butylhydroxylamine → alpha-[2-(4Methoxyphenylthio)-5-furyl]-N-tert-butylnitrone

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Reaction Steps

2-(4-Methoxyphenylthio)-5-furaldehyde (24.50 g) was mixed with N-tert-butylhydroxylamine (15.0 g, 168.16 mmol), molecular sieves (100 g) and silica gel (20 g) in CDCl3 (500 mL). The mixture was refluxed overnight under argon gas, and then filtered and concentrated on a rotary evaporator. The residue was recrystallized from hexanes (435 mL) to afford the title compound as yellowish crystals (27.52 g, yield 78.8%), m.p. 91.7° C. (Rf=0.15 on a silica gel plate using hexanes/EtOAc, 2:1, v:v, as the eluant).

Provenance & Evidence