Sodium Azide → 4-Azido-1-(4-methoxyphenyl)butan-1-one

HRID 2250476Notes

Reaction equation

HRID 2250476 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6].[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C>[N:15]([CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6])=[N+:16]=[N-:17]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 964144-Chloro-4'-methoxybutyrophenone

Product 1

HCID 596419724-Azido-1-(4-methoxyphenyl)butan-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-chloro-4′-methoxybutyrophenone (Acros Organics) (22.45 g, 106 mmol) in DMF (300 mL) was added sodium azide (13.7 g, 211 mmol). The solution was heated under N2 (g) at 70° C. for 4 h. The milky reaction mixture was partitioned between ethyl acetate (700 mL) and water (500 mL). The organic layer was washed with another portion of water (500 mL), followed by saturated aqueous sodium bicarbonate (500 mL) and brine (500 mL). The organic layer was dried (sodium sulfate) and concentrated to give an oil (22 g, 95% yield) which solidifed slowly upon standing. MS m/e 220; HPLC retention time 3.09 min.

Workup

  1. customThe milky reaction mixture
  2. customwas partitioned between ethyl acetate (700 mL) and water (500 mL)
  3. washThe organic layer was washed with another portion of water (500 mL)
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a2e745d4bab247858538cf72e8be8339
Source dataset
uspto-grants-2008_01
Patent number
US07317032B2

Reaction notes

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