Methanol → HCID 178510745, compound

HRID 659660Notes

Reaction equation

HRID 659660 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Cl.[NH2:12][OH:13].C(=O)(O)[O-].[Na+].CO.O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:12][OH:13])=[NH:10])=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 27914Benzeneacetonitrile, 4-bromo-HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 178510745HCID 178510745, compoundYield 85.6%

Procedure

4-Bromophenylacetonitrile (5.0 g, 25.5 mmol), hydroxylamine hydrochloride (3.9 g, 56.1 mmol), and sodium bicarbonate (5.1 g, 61.2 mmol) were dissolved in MeOH (250 mL, 6.2 mol) and water (40 mL, 2 mol). The mixture was heated at reflux overnight, cooled, and then concentrated to ˜50 mL. The residue was dissolved in DCM, washed with water and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to yield 2-(4-bromophenyl)-N-hydroxyacetamidine (5.0 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. concentrationconcentrated to ˜50 mL
  5. dissolutionThe residue was dissolved in DCM
  6. washwashed with water and saturated aqueous NaCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-bcf971a5982742f3b1319bff049a5f56
Source dataset
uspto-grants-2011_12
Patent number
US08080572B2

Reaction notes

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