Sodium Azide → HCID 178420709, compound

HRID 345926Notes

Reaction equation

HRID 345926 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 precipitate collected, triturated with water, filtered and lyophilized 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 precipitate collected
  4. customtriturated with water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7ddd4e6e443f470a91b192cfbb89341d
Source dataset
uspto-grants-1991_10
Patent number
US05059610

Reaction notes

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