4-Fluorophenyl isocyanate → HCID 9928435, compound

HRID 2105260Notes

Reaction equation

HRID 2105260 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[N:11]1([CH:16]([C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)[CH:17]([CH3:19])[CH3:18])[CH:15]=[CH:14][N:13]=[CH:12]1>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:26][C:23]2[CH:24]=[CH:25][C:20]([CH:16]([N:11]3[CH:15]=[CH:14][N:13]=[CH:12]3)[CH:17]([CH3:19])[CH3:18])=[CH:21][CH:22]=2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 22335511HCID 22335511, compound

Product 1

HCID 9928435HCID 9928435, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Fluorophenylisocyanate (0.017 mol) was added to a solution of 4-[1-(1H-imidazol-1-yl)-2-methylpropyl]benzenamine (0.014 mol) in dry THF (100 ml) and the mixture was stirred and refluxed for 2 hours. The mixture was cooled, the precipitate was filtered off and recrystallized from 2-propanone and CH3OH, yielding 1.6 g (32%) (±)—N-(4-fluorophenyl)-N′-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]phenyl]urea (compound 740).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe mixture was cooled
  3. filtrationthe precipitate was filtered off
  4. customrecrystallized from 2-propanone and CH3OH

Sources & evidence

ORD record
ord-cb01ff809506429fa33400364885a87d
Source dataset
uspto-grants-2009_08
Patent number
US07579352B2

Reaction notes

Loading…