Ethanol → N-Hydroxy-2-(3-iodo-phenyl)-acetamidine

HRID 1161144Notes

Reaction equation

HRID 1161144 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[I:7][C:8]1[CH:9]=[C:10]([CH2:14][C:15]#[N:16])[CH:11]=[CH:12][CH:13]=1.Cl.[NH2:18][OH:19].CCO>O>[OH:19][NH:18][C:15](=[NH:16])[CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([I:7])[CH:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 27593682-(3-Iodophenyl)acetonitrile

Product 1

HCID 178510804N-Hydroxy-2-(3-iodo-phenyl)-acetamidineYield 96.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Add sodium carbonate (2.0 g, 18.5 mmol) to a mixture of 3-iodophenylacetonitrile (4.5 g, 18.5 mmol) and hydroxylamine hydrochloride (1.3 g, 18.5 mmol) in 10:1 EtOH:H2O (11 mL). Heat the reaction mixture to 50° C. for 2 days. Cool to RT, then filter to remove the solids. Concentrate the filtrate to afford the title compound (4.94 g). LC-MS (m/e): 277 (M+1).

Workup

  1. temperatureCool to RT
  2. filtrationfilter
  3. customto remove the solids
  4. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-39ae7a286b9c40f7aeae920bfbcf36e1
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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