Ceric ammonium nitrate → HCID 21919183, compound

HRID 1245221Notes

Reaction equation

HRID 1245221 reaction equation
C[O:2][C:3]1[C:4]([CH3:41])=[C:5]([C:32]([O:39]C)=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[C:11]([CH:25]=1)[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1)=[O:13].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>C(#N)C.O>[CH3:36][O:35][C:34]1[C:3](=[O:2])[C:4]([CH3:41])=[C:5]([CH2:6][C:7]2[CH:8]=[CH:9][C:10]([C:26]3[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=3)=[C:11]([CH:25]=2)[C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:19][CH:20]=2)=[O:13])[C:32](=[O:39])[C:33]=1[O:37][CH3:38]

Participants

5

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 21919109HCID 21919109, compound

Product 1

HCID 21919183HCID 21919183, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

N-[5-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(4-pyridyl)benzoyl]-4-trifluoromethylaniline (140 mg, 0.2473 mmol) was dissolved in a mixed solvent of acetonitrile (9 ml) and water (3 ml), then CAN (399 mg, 0.7416 mmol) was added thereto at room temperature and the mixture was stirred for 3 hours. The reaction solution was poured into water and extracted with ethyl acetate. The extract was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by preparative thin layer chromatography (methylene chloride:methanol=95:5) to give the title compound (60 mg, 0.1119 mmol, 45%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated
  5. customThe residue was purified by preparative thin layer chromatography (methylene chloride:methanol=95:5)

Sources & evidence

ORD record
ord-a023e974b5744bb09c24da3e2fa799f5
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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