Benzonitrile, 4-bromo- → 4-Bromo-N'-hydroxybenzene-1-carboximidamide

HRID 1003702Notes

Reaction equation

HRID 1003702 reaction equation
CC(C)([O-])C.[K+].Cl.[NH2:8][OH:9].[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1>CO>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([C:15](=[N:8][OH:9])[NH2:16])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 12162Benzonitrile, 4-bromo-HCID 443297Hydroxyamine hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 27568384-Bromo-N'-hydroxybenzene-1-carboximidamideYield 109.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of ice cooled methanol (115 ml), under argon, was added potassium tert-butoxide (10.12 g. 0.09 mol), portionwise. After stirring for 5 minutes hydroxylamine hydrochloride (6.71 g, 0.097 mol) was added in one portion. After stirring for 1 hour at room temperature a slurry of 4-bromobenzonitrile, (10.88 g, 0.06 mol) in methanol (150 ml) was added. The mixture was then heated at reflux for 4 hours, cooled and filtered. The filtrate was evaporated in vacuo to give the title compound as a colourless solid (14.12 g, quant.)

Workup

  1. additionwas added in one portion
  2. additionwas added
  3. temperatureThe mixture was then heated
  4. temperatureat reflux for 4 hours
  5. temperaturecooled
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-547bb660837142f3bb24e7a104d35fd1
Source dataset
uspto-grants-2000_04
Patent number
US06046210

Reaction notes

Loading…