Ethanol → N-Hydroxy-4-iodo-benzamidine

HRID 861409Notes

Reaction equation

HRID 861409 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Cl.[NH2:17][OH:18].C(O)C>O>[I:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[N:17][OH:18])[NH2:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 764674-IodobenzonitrileHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 4429393N-Hydroxy-4-iodo-benzamidineYield 67.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-iodobenzonitrile (7.69 g), anhydrous sodium carbonate (6.25 g), hydroxylamine hydrochloride (8.74 g), in water (60 ml) and sufficient ethanol to maintain a clear solution, was heated at 90°-100° C. for 4 hours. The reaction mixture was cooled to ambient temperature and evaporated until a precipitate formed. The solid was collected by filtration, washed with water and recrystallised from acetonitrile to give 4-iodobenzamidoxime (5.97 g), m.p. 155°-161° C.; microanalysis, found: C, 31.4; H, 2.7; N, 10.2%; C7H7IN2 O 0.2H2O requires: C, 31.6; H, 2.81; R, 10.5%; NMR: 5.82(2H,s), 7.46(2H,d), 7.73(2H,d), 9.69(1H,s); m/z 263(M+H).

Workup

  1. temperaturewas heated at 90°-100° C. for 4 hours
  2. customevaporated until a precipitate
  3. customformed
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-58e286e0c6174a19bee6f055c91467ed
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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