Water → HCID 18331085, compound

HRID 2270053Notes

Reaction equation

HRID 2270053 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:15])[CH2:13]Br)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[N-:16]=[N+:17]=[N-:18].[Na+].O>CN(C)C=O>[N:16]([CH2:13][C:12]([C:9]1[CH:10]=[CH:11][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=1)=[O:15])=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 11966043Ethyl 4-(2-bromoacetyl)benzoate

Product 1

HCID 18331085HCID 18331085, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4′-ethoxycarbonyl-2-bromoacetophenone (2.0 g) in N,N-dimethylformamide (8 ml) was added sodium azide (480 mg) at 0° C., and stirred for 2 hours at room temperature. The reaction mixture was poured into water (100 ml), extracted with diethyl ether (200 ml×2), washed with brine, and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The product was purified by silica gel column chromatography (ethyl acetate:hexane=1:5) to give 2-azido-4′-ethoxycarbonylacetophenone (1.46 g).

Workup

  1. extractionextracted with diethyl ether (200 ml×2)
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationMagnesium sulfate was filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe product was purified by silica gel column chromatography (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-0826fe863e664bf7a30270f5d657859b
Source dataset
uspto-grants-2001_12
Patent number
US06331521B1

Reaction notes

Loading…