Acetone → HCID 53679379, compound

HRID 963609Notes

Reaction equation

HRID 963609 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].C1(C)C=CC=CC=1.CC(C)=O.[N-:25]=[N+:26]=[N-:27].[Na+]>O.CC(C)=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([N:25]=[N+:26]=[N-:27])=[O:8]

Participants

7

Reactant 4

HCID 180AcetoneHCID 1140TolueneHCID 33557Sodium AzideHCID 156548685-Fluoro-2-nitrobenzoyl chloride

Product 1

HCID 53679379HCID 53679379, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of 5-fluoro-2-nitrobenzoyl chloride (52 g, 0.256 mol) in a toluene (50 mL) and acetone (60 mL) mixture is added dropwise to a solution of sodium azide (19.55 g, 0.301 mol) in water while maintaining the reaction mixture temperature below 30° C. The resultant solid is collected and the filtrate is extracted with ether. The organic extracts are combined, washed with water, dried over anhydrous magnesium sulfate and concentrated by blowing air over the solution to obtain additional solids. The solids are combined, slurried in an acetone/water (1:3) solution, filtered and dried to give the title product as a yellow solid.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature below 30° C
  2. customThe resultant solid is collected
  3. extractionthe filtrate is extracted with ether
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customto obtain additional solids
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-3309aa47fd59404eb0d3f8b66cf01e88
Source dataset
uspto-grants-1998_06
Patent number
US05763605

Reaction notes

Loading…