Hydroxyamine hydrochloride → HCID 178513292, compound

HRID 1770202Notes

Reaction equation

HRID 1770202 reaction equation
[OH:1][C:2]1[C:9]([CH2:10][C:11]2[N:12]=[CH:13][NH:14][CH:15]=2)=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>CO>[OH:18][NH:17][C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][C:11]2[N:12]=[CH:13][NH:14][CH:15]=2)[C:2]=1[OH:1])=[NH:5]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 178509731HCID 178509731, compound

Product 1

HCID 178513292HCID 178513292, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 g (0.015 mole) of 2-hydroxy-3-(1H-imidazol-4-ylmethyl-)benzonitrile (prepared in example 1.1 above) are dissolved in 100 ml of methanol and 1.15 g (0.0165 mole) of hydroxylamine hydrochloride and 1.84 g of sodium acetate are added thereto. The resulting mixture is then heated at the reflux temperature for 20 hours. The methanol is evaporated under reduced pressure and the residue is taken up in 100 ml of water. The resulting aqueous solution is neutralized to pH 7 by addition of an aqueous sodium bicarbonate solution. The white precipitate thus formed is filtered off, dried under vacuum and recrystallized from methanol. 1.6 g of N,2-dihydroxy-3-(1H-imidazol-4-ylmethyl)-benzenecarboximidamide, identical to the product obtained in example 2.5 above, are obtained. Yield 46%.

Workup

  1. temperatureThe resulting mixture is then heated at the reflux temperature for 20 hours
  2. customThe methanol is evaporated under reduced pressure
  3. additionThe resulting aqueous solution is neutralized to pH 7 by addition of an aqueous sodium bicarbonate solution
  4. customThe white precipitate thus formed
  5. filtrationis filtered off
  6. customdried under vacuum
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-de5cd89cd7e54e00b944a70ebc1db417
Source dataset
uspto-grants-1995_01
Patent number
US05385927

Reaction notes

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