Water → 4-Azidobutyrophenone

HRID 2189927Notes

Reaction equation

HRID 2189927 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[N-:13]=[N+:14]=[N-:15].[Na+].O>CS(C)=O>[N:13]([CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])=[N+:14]=[N-:15]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 2535334-Chlorobutyrophenone

Product 1

HCID 108779184-AzidobutyrophenoneYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 4-chloro-1-phenylbutan-1-one (26.4 mL, 164 mmol) in DMSO (200 mL) was added sodium azide (12.8 g, 197 mmol). The solution was warmed to 55° C. and stirred for 16 hours. The cooled mixture was then treated with water and extracted with ether. The combined organics were washed with water and brine, then dried over MgSO4 and concentrated to provide the product as an orange oil (30.7 g, 99%).

Workup

  1. extractionextracted with ether
  2. washThe combined organics were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e025eabfe0ad4159a04a651cf08adc38
Source dataset
uspto-grants-2012_12
Patent number
US08324257B2

Reaction notes

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