Ammonium Hydroxide → 1-(3-Cyanophenyl)urea

HRID 272781Notes

Reaction equation

HRID 272781 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[OH-].[NH4+:13]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:13])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 27333153-Isocyanatobenzonitrile

Product 1

HCID 206364711-(3-Cyanophenyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-cyanophenyl isocyanate (1.0 g, 6.90 mmol) in THF (5 mL), ammonium hydroxide (1.7 mL, 13.8 mmol) was added. The reaction was stirred for 2 h at rt. The solvent was evaporated and the crude residue was redissolved in ethyl acetate. The organic layer was washed with water and brine and dried over sodium sulfate. The solvent was evaporated and the crude residue was purified by flash column chromatography to 41A (0.37 g).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude residue was redissolved in ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated
  6. customthe crude residue was purified by flash column chromatography to 41A (0.37 g)

Sources & evidence

ORD record
ord-cc36db0608964e15b7d2f4c53ebf0783
Source dataset
uspto-grants-2008_11
Patent number
US07456195B2

Reaction notes

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