Phenyl isocyanate → N-(4-cyanopheny)-N-(1H-imidazol-1-yl)-N'-phenylurea

HRID 446172Notes

Reaction equation

HRID 446172 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:10]1([NH:15][C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=2)[CH:14]=[CH:13][N:12]=[CH:11]1>C1COCC1>[C:20]([C:19]1[CH:18]=[CH:17][C:16]([N:15]([N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)[C:8]([NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:9])=[CH:23][CH:22]=1)#[N:21]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 230181884-[(1H-imidazol-1-yl)amino]benzonitrile

Product 1

HCID 69455384N-(4-cyanopheny)-N-(1H-imidazol-1-yl)-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Phenyl isocyanate (3.6 ml, 32.6 mmol) was added to a solution of 4-[N-(1H-imidazol-1-yl)amino]benzonitrile (5 g, 27.17 mmol) in THF (50 ml). The mixture was stirred at 50° C. overnight and after evaporation was crystallised in acetone/EtOH to give white crystals (2.5 g, 30.3%, 178° C.).

Workup

  1. customafter evaporation
  2. customwas crystallised in acetone/EtOH
  3. customto give white crystals (2.5 g, 30.3%, 178° C.)

Sources & evidence

ORD record
ord-9d739387e3b6469f8c4a265973962a77
Source dataset
uspto-grants-2013_07
Patent number
US08476455B2

Reaction notes

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