4-Chlorophenyl Isocyanate → N-(4-chlorophenyl)-N'-[4-(2-chlorophenyl)-1,2-dihydro-1,6,7-trimethyl-2-oxo-3-quinolyl]urea

HRID 1588731Notes

Reaction equation

HRID 1588731 reaction equation
[NH2:1][C:2]1[C:3](=[O:22])[N:4]([CH3:21])[C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[CH:9][C:8]([CH3:19])=[C:7]([CH3:20])[CH:6]=2.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[O:32])=[CH:26][CH:25]=1>C1C=CC=CC=1>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:1][C:2]2[C:3](=[O:22])[N:4]([CH3:21])[C:5]3[C:10]([C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:9][C:8]([CH3:19])=[C:7]([CH3:20])[CH:6]=3)=[O:32])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 197544703-amino-4-(2-chlorophenyl)-1,6,7-trimethyl-2(1H)-quinolone

Product 1

HCID 54113676N-(4-chlorophenyl)-N'-[4-(2-chlorophenyl)-1,2-dihydro-1,6,7-trimethyl-2-oxo-3-quinolyl]ureaYield 80.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-amino-4-(2-chlorophenyl)-1,6,7-tri-methyl-2(1H)-quinolone (156 mg), 4-chlorophenyl isocyanate (115 mg) and benzene (4 ml) was refluxed for 1.5 hours and then distilled to remove the solvent. The remaining crystals as collected by filtration were washed with isopropyl ether to obtain N-(4-chlorophenyl)-N'-[4-(2-chlorophenyl) -1,2-dihydro-1,6,7-trimethyl-2-oxo-3-quinolyl]urea (188 mg, 80.7%). Recrystallization from acetone - hexane gave colorless needles. mp 207°-209° C.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. distillationdistilled
  3. customto remove the solvent
  4. filtrationThe remaining crystals as collected by filtration
  5. washwere washed with isopropyl ether

Sources & evidence

ORD record
ord-4e2d530742674a908b1adf5ecaaab02d
Source dataset
uspto-grants-1993_06
Patent number
US05223513

Reaction notes

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