Sodium Azide → HCID 178420709, compound

HRID 2074021Notes

Reaction equation

HRID 2074021 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:26]=[CH:27][CH:28]=1)[O:16][CH2:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.[N-:29]=[N+:30]=[N-:31].[Na+].Cl.[NH+]1C=CC=CC=1>CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:26]=[CH:27][CH:28]=1)[O:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]2[NH:31][N:30]=[N:29][N:23]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 14774146HCID 14774146, compoundHCID 21584435Pyridinium hydrochloride

Product 1

HCID 178420709HCID 178420709, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A slurry of 2.0 g (5.48 mmol) of 4-(3-(2-quinolinylmethyloxy)phenoxymethyl)benzonitrile, 1.78 g (27.4 mmol) of sodium azide, and 3.16 g (27.4 mmol) of pyridinium hydrochloride in 12 ml of dry DMF is stirred under nitrogen at 100° C. for 20 hrs. The reaction mixture is then cooled to room temperature and concentrated. The residue is taken up on 100 ml of 1N aqueous NaOH and the solution extracted with ether. The aqueous layer is acidified to pH 6 with 1N aqueous HCl, and the solid which precipitates collected, triturated with water, filtered and lyopholized to obtain 5-(4-(3-(2-quinolinylmethyloxy)phenoxymethyl)phenyl)tetrazole. (M.P. 91° C. dec.)

Workup

  1. concentrationconcentrated
  2. extractionthe solution extracted with ether
  3. customthe solid which precipitates
  4. customcollected
  5. customtriturated with water
  6. filtrationfiltered

Sources & evidence

ORD record
ord-448e76b0093044de9757bea19e816f1a
Source dataset
uspto-grants-1990_04
Patent number
US04920132

Reaction notes

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