Thionyl Chloride → 4-Chloro-7-nitroquinazoline hydrochloride

HRID 1384660Notes

Reaction equation

HRID 1384660 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 (J. Chem. Soc. 1950, 1104-1111) (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%). 1H NMR Spectrum: (DMSOd6) 8.26(dd, 1H); 8.36(d, 1H); 8.40(s, 1H); 8.42(dd, 1H) MS-ESI: 209 [MH]+

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-2b0e60f7a4394147bb4fc4eb96e5fe9e
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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