Phosphorus oxychloride → 4-Chloro-6-(1-imidazolyl)quinazoline

HRID 618670Notes

Reaction equation

HRID 618670 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]=[CH:11][NH:10][C:9]3=O)[CH:5]=[CH:4][N:3]=[CH:2]1.P(Cl)(Cl)([Cl:19])=O>CN(C=O)C>[Cl:19][C:9]1[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[CH:7]=2)[N:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1358228196-(1-Imidazolyl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 218478354-Chloro-6-(1-imidazolyl)quinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

6-(1-Imidazolyl)-3,4-dihydroquinazolin-4-one (1.0 g) was dissolved in phosphorus oxychloride (15 ml). DMF (2 drops) was added and the mixture was heated at reflux for 1 hour. The mixture was evaporated, the residue was dissolved in methylene chloride, washed with sodium bicarbonate solution and the organic layer was dried (MgSO4) and evaporated to give 4-chloro-6-(1-imidazolyl)quinazoline (0.36 g) which was used without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 hour
  3. customThe mixture was evaporated
  4. dissolutionthe residue was dissolved in methylene chloride
  5. washwashed with sodium bicarbonate solution
  6. dry with materialthe organic layer was dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-1f16da2b6cc943b9869ef9ee08c53377
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Reaction notes

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