Sodium Hydroxide → HCID 178419996, compound

HRID 2351871Notes

Reaction equation

HRID 2351871 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:23]=[CH:22][C:16]([O:17][CH2:18][CH2:19][C:20]#[N:21])=[CH:15][CH:14]=1.[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C)C=O>[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:23]=[CH:22][C:16]([O:17][CH2:18][CH2:19][C:20]2[NH:26][N:25]=[N:24][N:21]=2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 19844730HCID 19844730, compound

Product 1

HCID 178419996HCID 178419996, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 9.8 g (0.032 mol) of 3-[4-(2-quinolylmethyloxy)phenoxy]propionitrile, 6.36 g of sodium azide and 5.28 g of ammonium chloride is heated with 30 ml of dry dimethylformamide at 140° C. for 20 hours. The reaction mixture is poured onto ice, basified with 1N sodium hydroxide and extracted 2 times with ethyl acetate. The aqueous fraction is acidified with acetic acid. The product is filtered and washed with water. The crude product is crystallized from acetonitrile to give 5-[2-(4-(2-quinolylmethyloxy)phenoxy)ethyl]tetrazole.

Workup

  1. additionThe reaction mixture is poured onto ice
  2. extractionextracted 2 times with ethyl acetate
  3. filtrationThe product is filtered
  4. washwashed with water
  5. customThe crude product is crystallized from acetonitrile

Sources & evidence

ORD record
ord-333b46f937a047d8bfcaf0261619701f
Source dataset
uspto-grants-1989_10
Patent number
US04874769

Reaction notes

Loading…