Ammonium Chloride → HCID 178518710, compound

HRID 1936755Notes

Reaction equation

HRID 1936755 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][NH:7][C:6]2=[O:13])#[N:2].[Cl-].[NH4+].[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C)C=O.C(OCC)(=O)C>[NH:16]1[C:1]([C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[CH:8][NH:7][C:6]3=[O:13])=[N:2][N:18]=[N:17]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 1357038834-Hydroxyquinazoline-6-carbonitrile

Product 1

HCID 178518710HCID 178518710, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

6-Cyanoquinazolin-4-one (0.5 g) in dimethylformamide (5 ml) was treated with ammonium chloride (0.33 g) and sodium azide (0.38 g) and heated at 100° C. under nitrogen for 45 minutes. The resulting mixture was cooled, diluted with ethyl acetate and filtered. The filter cake was washed with dimethylformamide and ethyl acetate to give the title compound (0.56 g) as a cream solid; δH [2H6]DMSO 13.00(1H,bs), 8.70(1H,d), 8.40(1H,dd), 8.38(1H,bs), 8.05(1H,s), 7.68(1H,d); m/z (M−1+) 213.

Workup

  1. temperatureThe resulting mixture was cooled
  2. filtrationfiltered
  3. washThe filter cake was washed with dimethylformamide and ethyl acetate

Sources & evidence

ORD record
ord-b4053fd5b17343aca767fee04675ce17
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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