Sodium Azide → [4-(4-Azidobutyl)phenyl]acetic acid

HRID 81295Notes

Reaction equation

HRID 81295 reaction equation
[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14]OS(C)(=O)=O)=[CH:7][CH:6]=1)([OH:3])=[O:2].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C>[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][N:20]=[N+:21]=[N-:22])=[CH:7][CH:6]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 71405718(4-{4-[(Methanesulfonyl)oxy]butyl}phenyl)acetic acid

Product 1

HCID 22566167[4-(4-Azidobutyl)phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Compound 6 (6 g, 0.02 mol) was dissolved in 80 ml of dry DMF then sodium azide (1.8 g, 0.027 mol) was added. The suspension was stirred at 80° C. (oil bath) for 3 h. The solvent was then removed at reduced pressure and the residual oil was treated with CH2Cl2 (100 mL).

Workup

  1. customThe solvent was then removed at reduced pressure
  2. additionthe residual oil was treated with CH2Cl2 (100 mL)

Sources & evidence

ORD record
ord-307f19f4582f4697939f09d30235deab
Source dataset
uspto-grants-2014_09
Patent number
US08846688B2

Reaction notes

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