Acetonitrile → HCID 18348631, compound

HRID 2268525Notes

Reaction equation

HRID 2268525 reaction equation
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.[CH3:31][N:32]([CH3:63])[C:33](=[O:62])[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH:45]2[CH2:53][C:52]3[C:47](=[C:48]([O:60]C)[C:49]([O:58][CH3:59])=[C:50]([O:56][CH3:57])[C:51]=3[O:54]C)[CH2:46]2)=[CH:36][CH:35]=1>O>[CH3:63][N:32]([CH3:31])[C:33](=[O:62])[C:34]1[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH:45]2[CH2:53][C:52]3[C:51](=[O:54])[C:50]([O:56][CH3:57])=[C:49]([O:58][CH3:59])[C:48](=[O:60])[C:47]=3[CH2:46]2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 180504Ceric ammonium nitrateHCID 18348591HCID 18348591, compound

Product 1

HCID 18348631HCID 18348631, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A water (1.0 ml) solution of CAN (1.07 g, 1.96 mmols) was dropwise added to an acetonitrile (8.0 ml) solution of N,N-dimethyl-4-[4-(4,5,6,7-tetramethoxyindan-2-yl)butoxy]benzamide (358 mg, 0.782 mmols), with cooling with ice, and stirred for 15 minutes. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:2) followed by recrystallization (from diisopropyl ether-ethyl acetate) to obtain the entitled compound (153 mg) as crystals.

Workup

  1. temperaturewith cooling with ice
  2. extractionwas then extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, and then dried
  5. customThe solvent was evaporated out in vacuo
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:2)
  7. customfollowed by recrystallization (from diisopropyl ether-ethyl acetate)

Sources & evidence

ORD record
ord-efc67bb9cae04b6c95d14b6649550686
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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