Methanol → HCID 178510745, compound

HRID 250810Notes

Reaction equation

HRID 250810 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-63cf39fc596644ecaac044ae2bd50df8
Source dataset
uspto-grants-2011_01
Patent number
US07863309B2

Reaction notes

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