Sodium Azide → HCID 57976173, compound

HRID 420891Notes

Reaction equation

HRID 420891 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]([CH2:15]OS(C)(=O)=O)([CH3:14])[NH:10][C:9]2=[O:21])=[CH:4][C:3]=1[C:22]([F:25])([F:24])[F:23].[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C=O)C>[N:26]([CH2:15][C:11]1([CH3:14])[NH:10][C:9](=[O:21])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:22]([F:25])([F:23])[F:24])[CH:4]=2)[C:12]1=[O:13])=[N+:27]=[N-:28]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 57976191HCID 57976191, compound

Product 1

HCID 57976173HCID 57976173, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methanesulfonic acid 1-(4-chloro-3-trifluoromethyl-phenyl)-4-methyl-2,5-dioxo-imidazolidin-4-ylmethyl ester (1.0 g, 2.5 mmoL) from Example 11, NaN3 (1.6 g, 25 mmoL) and KI (40 mg, 0.25 mmoL) in DMF (8 mL) was heated at 100° C. for 10 hrs. The crude product was partitioned between ether and water. The organic layer was washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated, then purified by silica gel column chromatography using heptane and ethyl acetate as eluent to afford the title compound as a colorless oil (566 mg, yield 65%).

Workup

  1. customThe crude product was partitioned between ether and water
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-53c9692efa244ce4977ace43dca43a85
Source dataset
uspto-grants-2012_01
Patent number
US08097730B2

Reaction notes

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