Sodium Azide → HCID 17954492, compound

HRID 747223Notes

Reaction equation

HRID 747223 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([CH2:13]S([O-])(=O)=O)[O:10][N:9]=2)=[CH:4][C:3]=1[F:18].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C>[N:19]([CH2:13][CH:11]1[O:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([F:18])[CH:4]=2)[CH2:12]1)=[N+:20]=[N-:21]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86598068HCID 86598068, compound

Product 1

HCID 17954492HCID 17954492, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

[3-(4-Bromo-3-fluorophenyl)-4,5-dihydroisoxazol-5-yl]methane sulfonate (9.85 g, 28 mmol) was dissolved in dry DMF (100 ml). Sodium azide (2.73 g, 42 mmol) was added and the reaction mixture stirred at 80° C. for 5 hours. The reaction mixture was concentrated in vacuo then azeotroped with xylene (20 ml). The crude product was dissolved in ethyl acetate (100 ml) and washed with water (100 ml). The organic layer was separated, dried over magnesium sulfate, filtered then concentrated in vacuo to yield 8.046 g of the desired compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthen azeotroped with xylene (20 ml)
  3. dissolutionThe crude product was dissolved in ethyl acetate (100 ml)
  4. washwashed with water (100 ml)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-41f465db739142d984824fb4ac1d02c8
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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