Sodium Azide → HCID 16753951, compound

HRID 1726565Notes

Reaction equation

HRID 1726565 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11].[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O>[N:16]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[S:10]([N:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])=[N+:17]=[N-:18]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 16753950HCID 16753950, compound

Product 1

HCID 16753951HCID 16753951, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
57.5 °C

Procedure

A mixture of intermediate 46, 2-bromomethyl-5-fluoro-N,N-dimethyl-benzenesulfonamide, (880 mg, 2.97 mmol) and sodium azide (200 mg, 3 mmol) in dimethylformamide (4 mL) was stirred at 55-60° C. for 30 min after which the solvent was removed in vacuo. The residue was partitioned between CH2Cl2 and water, and the organic phase was washed with water, dried (Na2SO4), filtered and concentrated to provide 670 mg (Yield 87%) of the title compound as a yellow oil; 1H NMR (500 MHz, CDCl3) δ ppm: 2.84 (6H, s) 4.78 (2H, s) 7.29-7.34 (1H, m) 7.59-7.64 (2H, m).

Workup

  1. customwas removed in vacuo
  2. customThe residue was partitioned between CH2Cl2 and water
  3. washthe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-009335020dfa43e2beb4a2c2f9732835
Source dataset
uspto-grants-2009_02
Patent number
US07491819B1

Reaction notes

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