Acetone → HCID 53679379, compound

HRID 1451167Notes

Reaction equation

HRID 1451167 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-0796182c057742c9962f75c149f45f08
Source dataset
uspto-grants-1997_02
Patent number
US05604180

Reaction notes

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