Sodium Azide → HCID 23044225, compound

HRID 2165159Notes

Reaction equation

HRID 2165159 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][CH:13]([CH2:17]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:14]2)=[CH:9][CH:8]=1>O.C(O)C>[CH3:5][O:6][C:7]1[CH:16]=[C:15]2[C:10]([CH2:11][CH2:12][CH:13]([CH2:17][N:1]=[N+:2]=[N-:3])[CH2:14]2)=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 11210176p-Toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester

Product 1

HCID 23044225HCID 23044225, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3.9 g of sodium azide in 10 ml of water is added to a solution of 13.86 g (40 mmol) of p-toluenesulphonic acid (7-methoxy-1,2,3,4-tetrahydro-naphth-2-ylmethyl) ester in 200 ml of ethanol and the whole is boiled under reflux for 18 hours. After cooling, the alcohol is evaporated off under reduced pressure, water is added to the residue and extraction is carried out with dichloromethane. The organic phase is washed with water, dried over sodium sulphate and concentrated by evaporation. (7-methoxy-1,2,3,4-tetrahydro-naphth-2-yl)methylazide is obtained in the form of a yellow oil.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling
  3. customthe alcohol is evaporated off under reduced pressure, water
  4. additionis added to the residue and extraction
  5. washThe organic phase is washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5d76f36805e24074808e522c6fd94208
Source dataset
uspto-grants-1990_07
Patent number
US04939160

Reaction notes

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