Ammonium Chloride → HCID 178420505, compound

HRID 2422269Notes

Reaction equation

HRID 2422269 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21]#[N:22])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[O:1]([C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[CH2:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][C:21]2[NH:28][N:27]=[N:26][N:22]=2)=[CH:17][CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 23082906HCID 23082906, compound

Product 1

HCID 178420505HCID 178420505, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(4-((3-phenoxybenzyl)oxy)phenyl)propanenitrile (0.5 g, 1.52 mmol), sodium azide (0.49 g, 7.54 mmol) and ammonium chloride (0.41 g, 7.66 mmol) in N,N-dimethylformamide (20 ml) was stirred at 110° C. for 28 hrs. The reaction solution was diluted with ethyl acetate, washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography (ethyl acetate:hexane=2:3-2:1) to give an oil, which was crystallized from ethyl acetate-tetrahydrofuran to give the title compound (0.24 g, 43%).

Workup

  1. washwashed successively with aqueous citric acid solution, water and aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give an oil, which
  5. customwas crystallized from ethyl acetate-tetrahydrofuran

Sources & evidence

ORD record
ord-762d259bc71540c88e689186c584088e
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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