Phenyl chloroformate → N,O-Bis-(phenoxycarbonyl)-hydroxylamine

HRID 413575

Reaction equation

HRID 413575 reaction equation
[C:1](=[O:4])([OH:3])[O-].[Na+].Cl.[NH2:7][OH:8].[C:9]1([O:15][C:16](Cl)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[O:3]([C:1]([NH:7][O:8][C:16]([O:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:17])=[O:4])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate2×

Product 1

HCID 10107329N,O-Bis-(phenoxycarbonyl)-hydroxylamineYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of sodium bicarbonate (21.5 g, 0.256 mol) in water (150 ml) at 0° C. was added hydroxylamine hydrochloride (8.8 g, 0.127 mol). The reaction mixture was tirred for 30 min. and phenylchloroformate (60 g, 0.383 mol) was introduced directly into the vigorously stirred mixture. Sodium bicarbonate (32.3 g, 3.85 mol) in water (300 ml) was added to the mixture. The mixture was stirred for 30 min., the ice-bath removed and stirring continued for an additional 2 h at room temperature. The resultant suspension was filtered and the filter cake washed with water. The wet filter cake was collected, suspended in hexane, filtered and again washed with hexane. The solid was kept at 0° C. overnight to afford N,O-bis-phenoxycarbonylhydroxylamine (23.5 g, 68%) as a solid. Melting point: 80-82° C. 1H NMR (CDCl3, 200 MHz): δ 7.26(m, 5H), 7.42 (m, 5H) and 8.54 (s, 1H).

Workup

  1. customthe ice-bath removed
  2. stirringstirring
  3. waitcontinued for an additional 2 h at room temperature
  4. filtrationThe resultant suspension was filtered
  5. washthe filter cake washed with water
  6. customThe wet filter cake was collected
  7. filtrationfiltered
  8. washagain washed with hexane
  9. waitThe solid was kept at 0° C. overnight

Sources & evidence

ORD record
ord-f4e30f4bede849dfb005ba3725dbd292
Source dataset
uspto-grants-2003_05
Patent number
US06566538B1

Linked notes

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