Hydroxyamine hydrochloride → HCID 86650740, compound

HRID 875201Notes

Reaction equation

HRID 875201 reaction equation
[CH3:1][C:2]1[C:6]([C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=O)=[CH:5][O:4][N:3]=1.Cl.[NH2:15][OH:16]>N1C=CC=CC=1>[OH:16][N:15]=[C:7]([C:6]1[C:2]([CH3:1])=[N:3][O:4][CH:5]=1)[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66887319HCID 66887319, compound

Product 1

HCID 86650740HCID 86650740, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (3-methyl-1,2-oxazol-4-yl)(2-thienyl)methanone (6.00 g, 31.0 mmol) and hydroxylamine hydrochloride (5.40 g, 77.6 mmol) in pyridine (80 mL) was stirred 5 h at 50° C. then overnight at room temperature. After removal of the solvent in vacuo, addition of water (50 mL) and extraction with ethyl acetate (3×40 mL), the combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was purified on silica gel to afford N-hydroxy-1-(3-methyl-1,2-oxazol-4-yl)-1-(2-thienyl)methanimine [6.45 g, yield 99%; HPLC/MS: m/z=219 (M+H); log P(HCOOH)=1.75].

Workup

  1. customovernight
  2. customat room temperature
  3. customAfter removal of the solvent
  4. additionin vacuo, addition of water (50 mL) and extraction with ethyl acetate (3×40 mL)
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-a8750d2110894b6190fca8bcef4a93aa
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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