Hydroxyamine hydrochloride → HCID 86650757, compound

HRID 875226Notes

Reaction equation

HRID 875226 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)=O)=[CH:5][N:4]=[CH:3]1.Cl.[NH2:15][OH:16]>N1C=CC=CC=1>[OH:16][N:15]=[C:7]([C:6]1[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=1)[C:9]1[CH:13]=[CH:12][S:11][CH:10]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66887902HCID 66887902, compound

Product 1

HCID 86650757HCID 86650757, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (1-methyl-1H-imidazol-5-yl)(3-thienyl)methanone (11.6 g, 60.0 mmol) and hydroxylamine hydrochloride (14.6 g, 210 mmol) in pyridine (60 mL) was stirred 9 h at 60° C. then left to stand for 72 h at room temperature. After removal of the solvent in vacuo, addition of water (200 mL), pH adjustment to approx 7 with aq. NaOH (1 M) induced precipitation of a solid. Filtration, sequential washings of the precipitate with water and heptane, and drying of the solid afforded a first crop of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-(3-thienyl)methanimine. The combined aqueous phases were extracted with dichloromethane, the combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified recrystallized from heptane to afford a second crop of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-(3-thienyl)methanimine. The crops were combined and recrystallized from diisopropylether to afford final N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-(3-thienyl)methanimine [9.95 g, yield 76%; HPLC/MS m/z=208 (M+H); log P(HCOOH)=0.21].

Workup

  1. waitthen left
  2. customAfter removal of the solvent
  3. additionin vacuo, addition of water (200 mL), pH adjustment to approx 7 with aq. NaOH (1 M)
  4. customprecipitation of a solid
  5. filtrationFiltration, sequential washings of the precipitate with water and heptane
  6. customdrying of the solid

Sources & evidence

ORD record
ord-9ef21242bbb64ecb829747c13f46474c
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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