Sodium Azide → HCID 86625618, compound

HRID 14508Notes

Reaction equation

HRID 14508 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13](F)=[CH:14][CH:15]=3)[O:10][C:9]=2[CH:20]([CH3:22])[CH3:21])=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C)C=O>[N:23]([C:13]1[CH:12]=[C:11]2[C:16]([C:17](=[O:18])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[C:9]([CH:20]([CH3:22])[CH3:21])[O:10]2)=[CH:15][CH:14]=1)=[N+:24]=[N-:25]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 686998323-(4-Chlorophenyl)-7-fluoro-2-isopropyl-chromen-4-one

Product 1

HCID 86625618HCID 86625618, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-(4-chlorophenyl)-7-fluoro-2-isopropyl-chromen-4-one (4.0 g, 12.7 mmol) in dry dimethylformamide (120 ml) is added sodium azide at room temperature. The reaction mixture is heated at 90° C. for 16 h, cooled to room temperature and partitioned between ethyl acetate and water. The organic phase is washed with water and brine, dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography on silica gel using iso-hexane:ethyl acetate (10:1) as the eluent, followed by recrystallisation from iso-hexane, gives the title compound.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel
  7. customfollowed by recrystallisation from iso-hexane

Sources & evidence

ORD record
ord-227e4f63db1f4277a6ca3bc5b60605a5
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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