Water → Phenyl N-hydroxycarbamate

HRID 1077680Notes

Reaction equation

HRID 1077680 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].Cl.[NH2:12][OH:13].C(=O)([O-])[O-].[K+].[K+].O>CCOCC>[C:5]1([O:4][C:2](=[O:3])[NH:12][OH:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 148233Phenyl N-hydroxycarbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Phenyl chloroformate (10 g, 63.8 mmol) in ether (10 mL) was added dropwise to a stirred mixture of finely ground hydroxylamine hydrochloride (63.8 mmol, 4.43 g) and potassium carbonate (58.4 mmol, 8.07 g) in ether (10 mL) containing water (1 mL) at 0° C. The mixture was stirred at room temperature for three days, filtered, and the solvent evaporated to give the Phenyl-N-hydroxycarbamate as crystals, m.p. 99.5°-100.7° C. (9.20 g, 94%).

Workup

  1. filtrationfiltered
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-6be59a1efa944e42b3fabc360180a0d8
Source dataset
uspto-grants-1996_08
Patent number
US05545507

Reaction notes

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