Sodium Azide → HCID 178466053, compound

HRID 2083234Notes

Reaction equation

HRID 2083234 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH:15]=[C:14]([C:17]#[N:18])[C:13](=[O:19])[C:12]=2[CH:20]=1)(=[O:7])[CH3:6].[N-:21]=[N+:22]=[N-:23].[Na+]>O1CCCC1>[C:5]([C:8]1[CH:20]=[C:12]2[C:11](=[CH:10][CH:9]=1)[O:16][CH:15]=[C:14]([C:17]1[NH:23][N:22]=[N:21][N:18]=1)[C:13]2=[O:19])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 137286106-Acetyl-4-oxo-4H-1-benzopyran-3-carbonitrile

Product 1

HCID 178466053HCID 178466053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 40 parts by volume of tetrahydrofuran are added under cooling 4.0 parts of anhydrous aluminum chloride, 3.20 parts of 6-acetyl-4-oxo-4H-1-benzopyran-3-carbonitrile and 2.93 parts of sodium azide in the order mentioned and, under stirring, the mixture is refluxed for 30 minutes. After cooled, the reaction mixture is concentrated to dryness. To the residue are added 100 parts by volume of 1N-hydrochloric acid and 3.10 parts of sodium nitrite, and the insoluble material is recovered by filtration and recrystallized four times from dimethylformamide to obtain 0.380 part of 6-acetyl-3-(1H-tetrazol-5-yl)-chromone as colorless crystals.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. temperatureAfter cooled
  3. concentrationthe reaction mixture is concentrated to dryness
  4. additionTo the residue are added 100 parts by volume of 1N-hydrochloric acid and 3.10 parts of sodium nitrite
  5. filtrationthe insoluble material is recovered by filtration
  6. customrecrystallized four times from dimethylformamide

Sources & evidence

ORD record
ord-6138a420df2348cebf0bdae768eb9a17
Source dataset
uspto-grants-1978_04
Patent number
US04085116

Reaction notes

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