Phenyl isocyanate → N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N'-phenylurea

HRID 387715Notes

Reaction equation

HRID 387715 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1(C)C=CC=CC=1>[C:17]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:19][CH2:20][CH2:21][O:22][CH3:23])[N:10]=[CH:9][CH:8]=[C:7]2[O:6][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:33]([NH:32][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:34])=[CH:25][CH:24]=1)#[N:18]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 229365064-(4-Aminophenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline

Product 1

HCID 22936365N-(4-(6-Cyano-7-(2-methoxyethoxy)-4-quinolyl)oxyphenyl)-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(4-Aminophenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline (600 mg) was suspended in toluene (15 ml), and the suspension was heated to reflux for dissolution, after which phenyl isocyanate (292 μl) was added dropwise and the mixture was heated to reflux for 30 minutes. After cooling, the precipitated solid was filtered out, washed with ether and ethyl acetate and dried to obtain 760 mg of the title compound.

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux for dissolution
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 30 minutes
  5. temperatureAfter cooling
  6. filtrationthe precipitated solid was filtered out
  7. washwashed with ether and ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-81348ff318e747c49d2db495c88c8302
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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