Ammonium Chloride → HCID 178439647, compound

HRID 978132Notes

Reaction equation

HRID 978132 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][C:7]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[C:13]#[N:14])=[C:6]([CH2:20][CH2:21][CH3:22])[C:5]=1[OH:23])(=[O:3])[CH3:2].[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+]>CN(C)C=O>[OH:23][C:5]1[C:6]([CH2:20][CH2:21][CH3:22])=[C:7]([O:8][CH2:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:12]([C:13]3[NH:26][N:25]=[N:24][N:14]=3)[CH:11]=2)[CH:18]=[CH:19][C:4]=1[C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13787721Benzonitrile, 3-[(4-acetyl-3-hydroxy-2-propylphenoxy)methyl]-

Product 1

HCID 178439647HCID 178439647, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8.25 g 3-[(4-acetyl-3-hydroxy-2-propyl phenoxy)methyl]benzonitrile, 5.20 g sodium azide and 4.30 g ammonium chloride in 125 mL anhydrous dimethylformamide was stirred and heated at 120° for 6 hr. The solvent was removed in vacuo and the residue was treated with 250 mL water and acidified with 10 mL 6N hydrochloric acid. The resulting solid was recrystallized from ethanol-water to give 7.78 g, mp 194°-195° of 1-[2-hydroxy-3-propyl-4-[[3-(1H-tetrazol-5-yl)phenyl]methoxy]phenyl]ethanone.

Workup

  1. temperatureheated at 120° for 6 hr
  2. customThe solvent was removed in vacuo
  3. additionthe residue was treated with 250 mL water
  4. customThe resulting solid was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-cad71e6610fa475db7fff5b70b5e3685
Source dataset
uspto-grants-1987_05
Patent number
US04663332

Reaction notes

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