Thionyl Chloride → 4-Chloro-7-nitroquinazoline hydrochloride

HRID 634723Notes

Reaction equation

HRID 634723 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8](=O)[NH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:17])=O>CN(C=O)C>[ClH:17].[Cl:17][C:8]1[C:7]2[C:12](=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[N:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 862228007-Nitroquinazolin-4(3H)-one

Product 1

HCID 226250614-Chloro-7-nitroquinazoline hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-nitro-3,4-dihydroquinazolin-4-one (5 g, 26 mmol) in thionyl chloride (50 ml) and DMF (1 ml) was heated at reflux for 1.5 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The residue was suspended in ether, collected by filtration and dried under vacuum to give 4-chloro-7-nitroquinazoline hydrochloride (6.4 g; 100%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. customExcess thionyl chloride was removed by evaporation
  4. customthe residue azeotroped with toluene
  5. filtrationcollected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-f7c7fc1cbd674afb975129d96a35e3ed
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

Loading…