Acetic Acid → HCID 178418666, compound

HRID 257455

Reaction equation

HRID 257455 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].C(O)(=O)C.[CH2:9]([O:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)CCC>[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]2[NH:22][N:3]=[N:2][N:1]=2)=[CH:23][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic Acid2×HCID 33557Sodium Azide2×HCID 5613714-Benzyloxybenzonitrile

Product 1

HCID 178418666HCID 178418666, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

6.6×10-2 mol of sodium azide and 6.6×10-2 mol of acetic acid were added to a solution of 5×10-2 mol of 4-benzyloxy benzonitrile (VIII) in 20 ml butanol. The reaction medium was then reflux-heated for 4 hours. 1 g sodium azide, 2 g acetic acid and 10 ml butanol were added and the reaction medium was again reflux-heated for 2 days. After concentration by evaporation of the solvent, the residue was dissolved in 20 ml of 10% aqueous NaOH. After filtration, the aqueous phase was extracted with ether. The alkaline solution was acidified with 2 N HCl to obtain the expected compound, which was isolated with an 85% yield (M.P.=228° C.).

Workup

  1. temperatureThe reaction medium was then reflux-heated for 4 hours
  2. temperaturethe reaction medium was again reflux-heated for 2 days
  3. concentrationAfter concentration
  4. customby evaporation of the solvent
  5. dissolutionthe residue was dissolved in 20 ml of 10% aqueous NaOH
  6. filtrationAfter filtration
  7. extractionthe aqueous phase was extracted with ether

Sources & evidence

ORD record
ord-2be1e4ba51b44926b20cef3614d53ed3
Source dataset
uspto-grants-1993_11
Patent number
US05262432

Linked notes

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