Benzophenone → HCID 22031937, compound

HRID 1792484Notes

Reaction equation

HRID 1792484 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([NH2:8])[CH:7]=1.[C:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:10](=[N:8][C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:9])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 3102BenzophenoneHCID 6101p-Toluenesulfonic acidHCID 27694075-Bromo-2-fluoroaniline

Product 1

HCID 22031937HCID 22031937, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

While a solution of 2.43 g 5-bromo-2-fluorophenylamine (compound in Production Example 335), 2.6 g benzophenone and 122 mg 4-toluenesulfonic acid in 50 ml toluene was azeotropically dehydrated, the mixture was heated for 6 hours under reflux. The reaction mixture was diluted with ethyl acetate and washed with brine, the organic layer was dried over anhydrous sodium sulfate, the solvent was removed, and the resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane) to give 1.91 g of the title compound (colorless oil).

Workup

  1. temperaturethe mixture was heated for 6 hours
  2. temperatureunder reflux
  3. washwashed with brine
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed
  6. customthe resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cbb7fc0bd2bb4f25abd04ac36e999884
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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