Water → 4-Azidobutyrophenone

HRID 468061Notes

Reaction equation

HRID 468061 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 (600 mL) and extracted with ether (3×200 mL). The combined organics were washed with water (8×100 mL) and brine (100 mL) then dried over MgSO4 and concentrated to provide the product as an orange oil (30.7 g, 99%).

Workup

  1. extractionextracted with ether (3×200 mL)
  2. washThe combined organics were washed with water (8×100 mL) and brine (100 mL)
  3. dry with materialthen dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e34272b51e1745f68fe9dde73ada8698
Source dataset
uspto-grants-2014_01
Patent number
US08623895B2

Reaction notes

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