Sodium Azide → 2'-acetyl-2-azido-N-methylacetanilide

HRID 48344Notes

Reaction equation

HRID 48344 reaction equation
[C:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[N:6]([CH3:11])[C:7](=[O:10])[CH2:8]Br)(=[O:3])[CH3:2].[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O.O>[C:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[N:6]([CH3:11])[C:7](=[O:10])[CH2:8][N:16]=[N+:17]=[N-:18])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 227422572'-acetyl-2-bromo-N-methylacetanilide

Product 1

HCID 227423952'-acetyl-2-azido-N-methylacetanilideYield 51.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.05 g (7.59 mmol) of 2′-acetyl-2-bromo-N-methylacetanilide and 2 g (30.77 mmol) of sodium azide were stirred in 20 ml of dimethylformamide at room temperature for 4 hours. The resulting mixture was diluted with water and extracted with diethyl ether. The organic phase was washed twice with water, dried over magnesium sulphate, evaporated to dryness and the residue chromatographed on silica gel using ethyl acetate/petrol 5:3 for the elution. There was obtained 910 mg of 2′-acetyl-2-azido-N-methylacetanilide as a colorless gum. MS: m/e 233 [M+H]+.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed twice with water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to dryness
  5. customthe residue chromatographed on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-90dbca10add4400988721a2a9294db4f
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

Loading…