Hydroxyamine hydrochloride → 5-Bromo-2-nitrothiophene-3-carbaldehyde oxime

HRID 1967147Notes

Reaction equation

HRID 1967147 reaction equation
[Br:1][C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([CH:10]=O)[CH:3]=1.Cl.[NH2:13][OH:14].C([O-])(=O)C.[Na+]>C(O)C>[Br:1][C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([CH:10]=[N:13][OH:14])[CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 534029475-Bromo-2-nitrothiophene-3-carbaldehyde

Product 1

HCID 723159975-Bromo-2-nitrothiophene-3-carbaldehyde oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Bromo-2-nitrothiophene-3-carbaldehyde (22.5 g, 95 mmol), hydroxylamine hydrochloride (6.96 g, 100 mmol) and sodium acetate (8.21 g, 100 mmol) were stirred in ethanol (225 mL) at room temperature overnight. The solvent was removed in vacuo, saturated NaHCO3 was added and the mixture extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as an orange solid.

Workup

  1. customThe solvent was removed in vacuo, saturated NaHCO3
  2. additionwas added
  3. extractionthe mixture extracted with EtOAc (3×)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d5fcbb4e8fa4402daa8c94dc8a261751
Source dataset
uspto-grants-2013_04
Patent number
US08420695B2

Reaction notes

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