m-Chloroperbenzoic acid → HCID 15035153, compound

HRID 1656424Notes

Reaction equation

HRID 1656424 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[C:13]([CH3:19])[CH:14]=[C:15]([CH3:18])[CH:16]=2)[N:11]=[CH:10][C:9]=1[NH:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31])=[O:22].ClC1C=CC=C(C(OO)=[O:40])C=1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:17]2[C:12](=[C:13]([CH3:19])[CH:14]=[C:15]([CH3:18])[CH:16]=2)[N+:11]([O-:40])=[CH:10][C:9]=1[NH:20][C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[F:31])=[O:22]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10048726HCID 10048726, compound

Product 1

HCID 15035153HCID 15035153, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-chlorophenyl)-3-[3-(2,4-difluoro-phenyl)ureido]- 6,8-dimethylquinoline (1.1 g), m-chloroperbenzoic acid (1.08 g) and dichloromethane (15 ml) was refluxed for 20 hrs. The reaction mixture was washed with aqueous sodium sulfite solution, aqueous sodium hydrogen carbonate solution and water, successively. After being dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was recrystallized from a mixture of methanol and chloroform to give 4-(2-chlorophenyl)-3-[3-(2,4-difluorophenyl)ureido]-6,8-dimethylquinoline 1-oxide as pale yellow prisms. Yield 0.72 g (63.2%). m.p. 230°-232° C.

Workup

  1. temperaturewas refluxed for 20 hrs
  2. washThe reaction mixture was washed with aqueous sodium sulfite solution, aqueous sodium hydrogen carbonate solution and water
  3. dry with materialAfter being dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was recrystallized from a mixture of methanol and chloroform

Sources & evidence

ORD record
ord-12b4df19ce634bb6856180915eacb312
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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