Sodium Azide → HCID 178476189, compound

HRID 2083228Notes

Reaction equation

HRID 2083228 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([O:8][CH:9]([C:11]1[CH:12]=[CH:13][C:14]2[O:19][CH:18]=[C:17]([C:20]#[N:21])[C:16](=[O:22])[C:15]=2[CH:23]=1)[CH3:10])(=[O:7])[CH3:6].[N-:24]=[N+:25]=[N-:26].[Na+]>O1CCCC1>[C:5]([O:8][CH:9]([C:11]1[CH:23]=[C:15]2[C:14](=[CH:13][CH:12]=1)[O:19][CH:18]=[C:17]([C:20]1[NH:26][N:25]=[N:24][N:21]=1)[C:16]2=[O:22])[CH3:10])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 203582201-(3-Cyano-4-oxo-4H-1-benzopyran-6-yl)ethyl acetate

Product 1

HCID 178476189HCID 178476189, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 45 parts by volume of tetrahydrofuran and 4.005 parts of anyhydrous aluminum chloride there are added 3.86 parts of 6-(1-acetoxyethyl)-4-oxo-4H-1-benzopyran-3-carbonitrile and 2.925 parts of sodium azide, and the resulting mixture is refluxed under stirring for 1.5 hours. After cooling, the solvent is distilled off. To the solid residue are added 2.1 parts of sodium nitrite and ice-water, and the mixture is well shaken. The insoluble material is recovered by filtration and recrystallized from ethyl acetate. The procedure yields 1.88 parts of 6-(1-acetoxyethyl)-3-(1H-tetrazol-5-yl)-chromone as colorless crystals. Melting point: 231°-232° C

Workup

  1. temperaturethe resulting mixture is refluxed
  2. temperatureAfter cooling
  3. distillationthe solvent is distilled off
  4. additionTo the solid residue are added 2.1 parts of sodium nitrite and ice-water
  5. stirringthe mixture is well shaken
  6. filtrationThe insoluble material is recovered by filtration
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d67c280d70b24789b79193fc546f1ed7
Source dataset
uspto-grants-1978_04
Patent number
US04085116

Reaction notes

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