N-tert-butylhydroxylamine → HCID 85059727, compound

HRID 850061Notes

Reaction equation

HRID 850061 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[S: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]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[S:11][C:12]([CH:15]=[N+:21]([C:17]([CH3:20])([CH3:19])[CH3:18])[O-:22])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 98586N-tert-butylhydroxylamineHCID 5023679HCID 5023679, compound

Product 1

HCID 85059727HCID 85059727, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(4-Methoxyphenylthio)-5-thiophenecarboxaldehyde from Step A was mixed with N-tert-butylhydroxylamine (10 g, 112.11 mmol), molecular sieves (4A, 50 g), silica gel (10 g) and chloroform (200 mL). The mixture was refluxed for 15 h, filtered and rotary evaporated. The residue obtained was purified by chromatography over silica gel eluting with hexanes/EtOAc (2:1, v:v) to provide a slightly pinkish powder (4.60 g, yield 16.8%), m.p.100.9° C. (Rf =0.19 on a silica gel plate using hexanes/EtOAc, 2:1, v:v, as the eluant).

Workup

  1. temperatureThe mixture was refluxed for 15 h
  2. filtrationfiltered
  3. customThe residue obtained
  4. customwas purified by chromatography over silica gel eluting with hexanes/EtOAc (2:1, v:v)

Sources & evidence

ORD record
ord-f0284f57530b4f7f911b8466a9d921e7
Source dataset
uspto-grants-2000_01
Patent number
US06015831

Reaction notes

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