Dichloromethane → Phenyl N-hydroxycarbamate

HRID 1582558Notes

Reaction equation

HRID 1582558 reaction equation
C([O-])(O)=O.[Na+].Cl.[NH2:7][OH:8].ClCCl.Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14]>O.C(OCC)(=O)C>[C:16]1([O:15][C:13](=[O:14])[NH:7][OH:8])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 15891Phenyl chloroformateHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 148233Phenyl N-hydroxycarbamateYield 78.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred solution of NaHCO3 (60.5 g) in water (200 mL) in a 2 L beaker was added portion-wise over 15 min 27.5 g of hydroxylamine hydrochloride. Once the bubbling subsided, dichloromethane (200 mL) was added to the reaction mixture and cooled to 5° C. Phenyl chloroformate (50 g) was then added at a steady rate to the reaction mixture. The reaction mixture was allowed to warm to room temperature and stirred for 1 h. Ethyl acetate (100 mL) was employed to bring the reaction mixture to a transparent solution. The organic layer was separated, washed with brine (200 mL) and dried over MgSO4. The organic solvent was removed under reduced pressure to give the title compound (38.20 g) as a white solid melting at 104-107° C.

Workup

  1. temperatureto warm to room temperature
  2. customThe organic layer was separated
  3. washwashed with brine (200 mL)
  4. dry with materialdried over MgSO4
  5. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-85240d107a9f4f3dbf974f68726f78ef
Source dataset
uspto-grants-2004_05
Patent number
US06737383B1

Reaction notes

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