Phenyl isocyanate → 1-Benzyloxy-1-(2-methylpropyl)-3-phenylurea

HRID 976627

Reaction equation

HRID 976627 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([O:17][NH:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH2:10]([O:17][N:18]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 19967392N-benzyloxy-N-(2-methylpropyl)amine

Product 1

HCID 199673831-Benzyloxy-1-(2-methylpropyl)-3-phenylureaYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenyl isocyanate (3.2 g, 27 mmol) was added via pipette to a solution of N-benyloxy-N-(2-methylpropyl)amine (4.8 g, 27 mmol) in methylene chloride (30 mL). The reaction mixture was allowed to stir at ambient temperature for 3 days. The solvent was removed under vacuum. The residue was purified by column chromatography (silica gel; 1:9 ethyl acetate:hexanes) to provide 6.2 g of 1-benzyloxy-1-(2-methylpropyl)-3-phenylurea as a white crystalline solid, m.p. 85°-87° C. Analysis: Calculated for C18H22N2 : %C, 72.46; %H, 7.43; %N, 9.39; Found: %C, 72.53; %H, 7.51; %N, 9.44.

Workup

  1. customThe solvent was removed under vacuum
  2. customThe residue was purified by column chromatography (silica gel; 1:9 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-a962be590707491a94d76263a5fb2fc5
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Linked notes

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