Hydroxyamine hydrochloride → HCID 178513388, compound

HRID 278494Notes

Reaction equation

HRID 278494 reaction equation
[CH3:1][O-:2].[Na+].Cl.[NH2:5][OH:6].OC[CH:9]([N:18]1[CH:22]=[C:21]([C:23]#[N:24])[N:20]=[CH:19]1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CO>[OH:6][NH:5][C:23]([C:21]1[N:20]=[CH:19][N:18]([CH:9]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:1][OH:2])[CH:22]=1)=[NH:24]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 54161502HCID 54161502, compound

Product 1

HCID 178513388HCID 178513388, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A powder of NaOMe (67.2 mg, 1.24 mmol) was added to a solution of hydroxylamine hydrochloride (86.4 mg, 1.24 mmol) in methanol (2 ml) at room temperature. After 30 minutes, 1-(1-hydroxy-4-phenyl-2-butyl)imidazole-4-carbonitrile (obtained in Example 12(2))(100 mg, 0.41 mmol) was added to the mixture and the resulting mixture was stirred at reflux for 2 h. After cooling, the insoluble material was removed and then the filtrate was evaporated. The residue was purified by silica gel (5 g) column chromatography eluting with chloroform/methanol (20:1) and concentrated in vacuo. The residue was triturated with isopropyl ether to give N-hydroxy-1-[1-hydroxy-4-phenyl-2-butyl]imidazole-4-carboximidamide (86.3 mg, 76.0%) as an amorphous solid.

Workup

  1. temperatureat reflux for 2 h
  2. temperatureAfter cooling
  3. customthe insoluble material was removed
  4. customthe filtrate was evaporated
  5. customThe residue was purified by silica gel (5 g) column chromatography
  6. washeluting with chloroform/methanol (20:1)
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with isopropyl ether

Sources & evidence

ORD record
ord-9a5950ae7144423c9750f42aa917606f
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

Loading…