Diethyl Ether → 1-(Benzyloxy)-3-phenylurea

HRID 976623

Reaction equation

HRID 976623 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OCC)C.[OH-].[Na+].[C:18]1([N:24]=[C:25]=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[CH2:2]([O:9][NH:10][C:25]([NH:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:26])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7672Phenyl isocyanateHCID 14798Sodium HydroxideHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 2542991-(Benzyloxy)-3-phenylureaYield 82.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a flask was charged sequentially with O-benzylhydroxylamine hydrochloride (37.5 g, 0.23 mole), water (40 mL) and diethyl ether (400 mL). The resulting mixture was cooled to 0° C. and a solution of sodium hydroxide (9.4 g, 0.23 mole) in water (40 mL) was added dropwise. After 0.5 hour, phenyl isocyanate (25.5 mL, 0.23 mole) was added. A white precipitate formed. The reaction was maintained at ambient temperature for 2 hours. The precipitate was isolated by filtration, washed with water and dried to provide 46.2 g of 1-benzyloxy-3-phenyl urea as a white crystalline solid.

Workup

  1. customA white precipitate formed
  2. temperatureThe reaction was maintained at ambient temperature for 2 hours
  3. customThe precipitate was isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-c598c63cadaa4ab8a72f2a539785d822
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Linked notes

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