Ammonium Chloride → 5-(6-chloro-5,7-dimethyl-4-oxo-4H-1-benzopyran-2-yl) tetrazole

HRID 1580697Notes

Reaction equation

HRID 1580697 reaction equation
[Cl:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]2[O:10][C:9]([C:11]#[N:12])=[CH:8][C:7](=[O:13])[C:6]=2[C:14]=1[CH3:15].[N-:17]=[N+:18]=[N-:19].[Na+].[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]2[O:10][C:9]([C:11]3[NH:19][N:18]=[N:17][N:12]=3)=[CH:8][C:7](=[O:13])[C:6]=2[C:14]=1[CH3:15]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 213926006-chloro-5,7-dimethyl-4-oxo-4H-1-benzopyran-2-carbonitrile

Product 1

HCID 1784223865-(6-chloro-5,7-dimethyl-4-oxo-4H-1-benzopyran-2-yl) tetrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 23.4 parts of 6-chloro-5,7-dimethyl-4-oxo-4H-1-benzopyran-2-carbonitrile, 7.8 parts of sodium azide, 6.4 parts of ammonium chloride and 200 parts of N,N-dimethylformamide was stirred and heated on the steam bath for 18 hours. Most of the solvent was then removed by distillation under reduced pressure. A solution of the residue in 400 parts of water was acidified with 20% hydrochloric acid. The precipitated solid was filtered off, washed with water and crystallized from dioxan to give 15.5 parts of 5-(6-chloro-5,7-dimethyl-4-oxo-4H-1-benzopyran-2-yl) tetrazole as a colourless solid, melting point 246-247°C (decomposition).

Workup

  1. temperatureheated on the steam bath for 18 hours
  2. customMost of the solvent was then removed by distillation under reduced pressure
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water
  5. customcrystallized from dioxan

Sources & evidence

ORD record
ord-2ece74329d304bf0ae9a9f4484a75d02
Source dataset
uspto-grants-1976_01
Patent number
US03933844

Reaction notes

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