Ammonium Chloride → HCID 178515422, compound

HRID 1112520Notes

Reaction equation

HRID 1112520 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][CH:4]=[C:3]1[C:12]#[N:13].[N-:14]=[N+:15]=[N-:16].[Na+].[Cl-].[NH4+]>CN(C)C=O>[NH:14]1[C:12]([C:3]2[C:2](=[O:1])[N:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]3=[N:5][CH:4]=2)=[N:13][N:16]=[N:15]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13480904HCID 13480904, compound

Product 1

HCID 178515422HCID 178515422, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 4-oxo-4H-pyrido[1,2-a]-pyrimidine-3-carbonitrile (2.17 g., 0.0127 mole), sodium azide (0.911 g., 0.014 mole), and ammonium chloride (0.75 g., 0.014 mole) in N,N-dimethylformamide (20 ml.) was heated by means of an oil bath maintained at 120° for 19 hours. The solvent was removed and the residue treated with hot aqueous sodium bicarbonate. The mixture was filtered. The filtrate was acidified with acetic acid. The precipitate was collected and recrystallized from acetic acid to give the title compound (0.52 g., 19%) m.p. 308°-309° (decomp). Recrystallization from acetic acid with charcoal treatment gave analytical material, m.p. 311°-312° (decomp).

Workup

  1. temperaturewas heated by means of an oil bath
  2. temperaturemaintained at 120° for 19 hours
  3. customThe solvent was removed
  4. additionthe residue treated with hot aqueous sodium bicarbonate
  5. filtrationThe mixture was filtered
  6. customThe precipitate was collected
  7. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-2c24545ebfa34e55a7aa5fddfada5bbb
Source dataset
uspto-grants-1978_10
Patent number
US04122274

Reaction notes

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