2,4-Difluorophenyl isocyanate → HCID 22936794, compound

HRID 1433359Notes

Reaction equation

HRID 1433359 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[N:31]=[C:32]=[O:33]>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][CH3:20])[N:10]=[CH:9][CH:8]=[C:7]2[O:6][C:5]1[CH:21]=[CH:22][C:2]([NH:1][C:32]([NH:31][C:25]2[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:24]=2[F:23])=[O:33])=[CH:3][CH:4]=1)#[N:18]

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 22936407HCID 22936407, compound

Product 1

HCID 22936794HCID 22936794, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(4-Aminophenoxy)-6-cyano-7-methoxyquinoline (180 mg) was added to 5.5 ml of toluene, and the mixture was heated to reflux. After then adding 2,4-difluorophenyl isocyanate (0.12 ml), the mixture was further heated to reflux for 1 hour. After cooling, the precipitated solid was filtered out and washed with ethyl acetate/toluene=1/1 to obtain 195 mg of the title compound as light brown crystals (70% yield).

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid was filtered out
  5. washwashed with ethyl acetate/toluene=1/1

Sources & evidence

ORD record
ord-826a5d6318164a6caa48b3a3e7d5cafa
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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