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

HRID 382448Notes

Reaction equation

HRID 382448 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[O:11][C:12]([CH:15]=O)=[CH:13][CH:14]=2)=[CH:5][CH:4]=1.[C:17]([NH:21][OH:22])([CH3:20])([CH3:19])[CH3:18]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9][C:10]2[O:11][C:12]([CH:15]=[N+:21]([C:17]([CH3:20])([CH3:19])[CH3:18])[O-:22])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 98586N-tert-butylhydroxylamineHCID 122305495-[(4-Methoxyphenyl)thio]-2-furancarboxaldehyde

Product 1

HCID 85074060alpha-[2-(4Methoxyphenylthio)-5-furyl]-N-tert-butylnitroneYield 86.2%

Procedure

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).

Workup

  1. temperatureThe mixture was refluxed overnight under argon gas
  2. filtrationfiltered
  3. concentrationconcentrated on a rotary evaporator
  4. customThe residue was recrystallized from hexanes (435 mL)

Sources & evidence

ORD record
ord-3d15129487e945aebe31a52079aafb93
Source dataset
uspto-grants-2001_10
Patent number
US06310092B1

Reaction notes

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