1-(1-Isocyanatoethyl)naphthalene → N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl)-N'-[1-(1-naphthyl)ethyl]urea

HRID 1857246Notes

Reaction equation

HRID 1857246 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1.[C:23]1([CH:33]([N:35]=[C:36]=[O:37])[CH3:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:36]([NH:35][CH:33]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[CH3:34])=[O:37])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6027531-(1-Isocyanatoethyl)naphthaleneHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Product 1

HCID 22132729N-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl)-N'-[1-(1-naphthyl)ethyl]ureaYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (54 mg) was dissolved in toluene (5 ml) with heat, 1-(1-naphthyl)ethyl isocyanate (0.05 ml) was added, and the admixture was refluxed with heat for 100 minutes. The resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 65 mg of the title compound (yield: 72%).

Workup

  1. temperaturewith heat
  2. temperaturethe admixture was refluxed
  3. temperaturewith heat for 100 minutes
  4. customThe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-4419428f36834e42b161cbb6e085f694
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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