Triethylamine → N,3-dihydroxybenzenecarboximidamide

HRID 1045370Notes

Reaction equation

HRID 1045370 reaction equation
Cl.[NH2:2][OH:3].C(N(CC)CC)C.[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16]>CS(C)=O.C1COCC1.O>[OH:3][N:2]=[C:15]([C:14]1[CH:17]=[CH:18][CH:19]=[C:12]([OH:11])[CH:13]=1)[NH2:16]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 133943-CyanophenolHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 54381771N,3-dihydroxybenzenecarboximidamide

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 15.84 g (0.228 mol) of hydroxylamine hydrochloride in 75 ml of DMSO there are added 32 ml (0.228 mol) of triethylamine. The solution is stirred vigorously for 30 minutes and is then diluted with a small amount of THF. After stirring for 10 minutes, the triethylamine hydrochloride is filtered off and the residue is rinsed with THF. After the filtrate has been concentrated (evaporating off the THF), 10 g (83.9 mmol) of 3-hydroxybenzonitrile are added to the solution obtained. The solution is stirred at ambient temperature for 16 hours. After diluting with cold water, the mixture is extracted 3 times with ethyl acetate and the organic phase is washed with brine. The expected product is obtained after drying over MgSO4 and evaporation.

Workup

  1. stirringAfter stirring for 10 minutes
  2. filtrationthe triethylamine hydrochloride is filtered off
  3. washthe residue is rinsed with THF
  4. concentrationAfter the filtrate has been concentrated (
  5. additionare added to the solution
  6. customobtained
  7. stirringThe solution is stirred at ambient temperature for 16 hours
  8. extractionthe mixture is extracted 3 times with ethyl acetate
  9. washthe organic phase is washed with brine

Sources & evidence

ORD record
ord-22ab0de0231f4c0ba0aa78f1f56de925
Source dataset
uspto-grants-2013_10
Patent number
US08569285B2

Reaction notes

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