Sodium Azide → 4-(4-Methoxyphenyl)butylazide

HRID 1294534Notes

Reaction equation

HRID 1294534 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:9][CH:8]=1>CN(C=O)C>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:1]=[N+:2]=[N-:3])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 110459014-(4-Methoxyphenyl)butyl 4-methylbenzene-1-sulfonate

Product 1

HCID 114994244-(4-Methoxyphenyl)butylazideYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Sodium azide (3.07 g, 0.047 mol) was added to a solution of 1 (12.9 g, 0.04 mol) in anhydrous DMF (70 mL) and the reaction mixture was stirred 12 h at 80° C. (oil bath). Then solvent was removed at reduced pressure and the residual oil was treated with a mixture of CH2Cl2/ether 3:1 (100 mL). The resulting solution was washed with water (2×100 mL), brine and dried over magnesium sulfate. The solvent was removed under reduced pressure and 7.6 g (95%) of 2 was obtained. The purity of 2 (99%) was determined by GC and TLC (eluent:hexane/ethyl acetate 1:1), Rf=0.84.

Workup

  1. customThen solvent was removed at reduced pressure
  2. additionthe residual oil was treated with a mixture of CH2Cl2/ether 3:1 (100 mL)
  3. washThe resulting solution was washed with water (2×100 mL), brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5d0e8e071af5437c80be938a45b228c4
Source dataset
uspto-grants-2007_07
Patent number
US07241766B2

Reaction notes

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