Phenyl isocyanate → HCID 13588450, compound

HRID 1285221Notes

Reaction equation

HRID 1285221 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]#[N:8].[C:9]1([N:15]=[C:16]=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(C(C)=O)C.C(O)C.C1(C)C=CC=CC=1>[C:9]1([NH:15][C:16]([NH:1][C:2]2[N:3]=[CH:4][NH:5][C:6]=2[C:7]#[N:8])=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 787775-amino-1H-imidazole-4-carbonitrile

Product 1

HCID 13588450HCID 13588450, compoundYield 40.9%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 21863594Toluene ethanolSolvent

Procedure

Under a nitrogen atmosphere a stirred solution of 4-amino-1H-imidazole-5-carbonitrile (1.1 g, 0.01 mole) and phenyl isocyanate (1.3 g, 0.011 mole) in 30 ml of dry methyl ethyl ketone was heated under reflux for 10 hours. The solvent was removed, and the residue was stirred with 50 ml of boiling tetrahydrofuran. The mixture was filtered hot, and the filtrate was concentrated under reduced pressure. The residual solid was slurried in 50 ml of diethyl ether and the solid was collected by filtration, washed three times with diethyl ether, and dried to give a solid (1.2 g; mp, 165° d). The solid was dissolved in hot ethanol/toluene and an insoluble material removed by filtration. The filtrate was concentrated under reduced pressure to give N-phenyl-N'-(5-cyano-1H-imidazol-4-yl)urea (0.93 g; mp, >300°).

Workup

  1. temperatureunder reflux for 10 hours
  2. customThe solvent was removed
  3. filtrationThe mixture was filtered hot
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. filtrationthe solid was collected by filtration
  6. washwashed three times with diethyl ether
  7. customdried
  8. customto give a solid (1.2 g; mp, 165° d)
  9. customan insoluble material removed by filtration
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-45d44e3bb7ef4fe59a298c2ffd2cb6a2
Source dataset
uspto-grants-1986_01
Patent number
US04565875

Reaction notes

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