Ammonium Chloride → HCID 178439418, compound

HRID 275377Notes

Reaction equation

HRID 275377 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[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>[C:1]([C:4]1[CH:19]=[CH:18][C:7]([CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]3[NH:26][N:25]=[N:24][N:15]=3)=[CH:12][CH:11]=2)=[C:6]([CH2:20][CH2:21][CH3:22])[C:5]=1[OH:23])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 137810304-(4-Acetyl-3-hydroxy-2-propylbenzyloxy)benzonitrile

Product 1

HCID 178439418HCID 178439418, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 19.0 g. of 4-(4-acetyl-3-hydroxy-2-propylbenzyloxy)benzonitrile, 13.0 g. of sodium azide, and 10.9 g. of ammonium chloride in 250 ml. of dimethylformamide was heated to 115° C. for eight hours. An additional 13.0 g. of sodium azide and 10.9 g. of ammonium chloride were added every 2.5 hours during this period. The reaction was stirred overnight at room temperature and then heated an additional six hours with more reagents being added. The reaction mixture was then evaporated under reduced pressure and the residue was dissolved in 800 ml. of water. The solution was made acidic with hydrochloric acid and the resulting precipitate was filtered. The precipitate was dissolved in 1N sodium hydroxide and the solution was washed once with ethyl acetate. The basic solution was made acidic with hydrochloric acid and the precipitate was recovered by filtration. The precipitate was crystallized first from isopropyl alcohol/ethyl acetate/water and then recrystallized from isopropyl alcohol providing 10.3 g. of the desired title product, m.p. 203°-205° C. IR, NMR.

Workup

  1. temperatureheated an additional six hours with more reagents
  2. additionbeing added
  3. customThe reaction mixture was then evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in 800 ml
  5. filtrationthe resulting precipitate was filtered
  6. dissolutionThe precipitate was dissolved in 1N sodium hydroxide
  7. washthe solution was washed once with ethyl acetate
  8. filtrationthe precipitate was recovered by filtration
  9. customThe precipitate was crystallized first from isopropyl alcohol/ethyl acetate/water
  10. customrecrystallized from isopropyl alcohol providing 10.3 g

Sources & evidence

ORD record
ord-5bb90b2cf915476f81a05ee0f44a6e9d
Source dataset
uspto-grants-1995_02
Patent number
US05393768

Reaction notes

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