Hydrochloric Acid → 5-Phenyl-2-tetrazol-5-yl-4H-pyran-4-one

HRID 1902655Notes

Reaction equation

HRID 1902655 reaction equation
[O:1]=[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][O:5][C:4]([C:14]#[N:15])=[CH:3]1.[N-:16]=[N+:17]=[N-:18].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[C:8]1([C:7]2[C:2](=[O:1])[CH:3]=[C:4]([C:14]3[NH:18][N:17]=[N:16][N:15]=3)[O:5][CH:6]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 130911754-oxo-5-phenyl-4H-pyran-2-carbonitrile

Product 1

HCID 1785158045-Phenyl-2-tetrazol-5-yl-4H-pyran-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-oxo-5-phenyl-4H-pyran-2-carbonitrile (2.0 g), sodium azide (1.0 g) and ammonium chloride (0.8 g) in dimethylformamide (20 ml) was stirred at room temperature for an hour. Ice (20 g) was added and the clear solution was acidified with 2 N hydrochloric acid (20 ml) giving a pale solid which was recrystallised from ethanol to give the title product (mp 237°-238° C. with decomposition).

Workup

  1. customgiving a pale solid which
  2. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-d7ba1ee261e442f28c933b54c8b63a06
Source dataset
uspto-grants-1982_12
Patent number
US04364956

Reaction notes

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