Ceric ammonium nitrate → HCID 69659126, compound

HRID 1745860Notes

Reaction equation

HRID 1745860 reaction equation
[CH2:1]([O:3][C:4]([C:6]12[CH2:27][C:7]1([CH:28]=[CH:29][CH2:30][CH2:31][CH3:32])[C:8]1[C:13]([N:14](CC3C=CC(OC)=CC=3)[C:15]2=[O:16])=[CH:12][CH:11]=[C:10]([Cl:26])[CH:9]=1)=[O:5])[CH3:2].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>[CH2:1]([O:3][C:4]([C:6]12[CH2:27][C:7]1([CH:28]=[CH:29][CH2:30][CH2:31][CH3:32])[C:8]1[C:13]([NH:14][C:15]2=[O:16])=[CH:12][CH:11]=[C:10]([Cl:26])[CH:9]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 180504Ceric ammonium nitrateHCID 69659052HCID 69659052, compound

Product 1

HCID 69659126HCID 69659126, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of 13 (31 mg, 0.068 mmol) in acetonitrile/H2O (9:1, 0.300 mL) was cooled to 0° C. in an ice-water bath and treated with CAN (112 mg, 0.204 mmol). The reaction mixture was stirred at ambient temperature for 12 h and quenched with Na2S2O5 to remove anisaldehyde. The resulting suspension was diluted with H2O, extracted with CH2Cl2, dried (Na2SO4), filtered, and concentrated in vacuo. Chromatography afforded 14 (14 mg, 60%) as a white solid.

Workup

  1. customquenched with Na2S2O5
  2. customto remove anisaldehyde
  3. additionThe resulting suspension was diluted with H2O
  4. extractionextracted with CH2Cl2
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e768c00a9344efab50745315d3f3b68
Source dataset
uspto-grants-2006_03
Patent number
US07019141B2

Reaction notes

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