P-Anisidine → N-4-methoxyphenyl-N'-cyano-O-phenylisourea

HRID 857905Notes

Reaction equation

HRID 857905 reaction equation
C1C=CC(O[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][C:10]#[N:11])=CC=1.[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>C(O)(C)C>[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:8](=[N:9][C:10]#[N:11])[O:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 688090Diphenyl N-Cyanocarbonimidate

Product 1

HCID 178492300N-4-methoxyphenyl-N'-cyano-O-phenylisoureaYield 69.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A slurry of diphenyl cyancarbonimidate (1 g) in isopropanol (10 mL) was treated with 4-methoxyaniline (517 mg). After stirring at room temperature for a further 2.5 hours the reaction mixture was filtered. The insoluble material was washed with isopropanol to give the title compound (778 mg) as a white solid, which was used without further purification.

Workup

  1. filtrationwas filtered
  2. washThe insoluble material was washed with isopropanol

Sources & evidence

ORD record
ord-c5d16a2e556b4d6f8942453347cd673f
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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