Thionyl Chloride → 4-Chloro-6-methoxy-7-nitroquinazoline hydrochloride

HRID 634742Notes

Reaction equation

HRID 634742 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[N:9]=[CH:8][NH:7][C:6]2=O.S(Cl)([Cl:19])=O>CN(C=O)C>[ClH:19].[Cl:19][C:6]1[C:5]2[C:10](=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 1354520046-Methoxy-7-nitroquinazolin-4(3H)-one

Product 1

HCID 212603064-Chloro-6-methoxy-7-nitroquinazoline hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-methoxy-7-nitro-3,4-dihydroquinazolin-4-one (8 g, 36 mmol) in thionyl chloride (150 ml) and DMF (0.8 ml) was heated at reflux for 3 hours. Excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The resulting solid was triturated with ether, collected by filtration and dried under vacuum to give 4-chloro-6-methoxy-7-nitroquinazoline hydrochloride(7.5 g, 75%).

Workup

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

Sources & evidence

ORD record
ord-126788b0e06043449c8eb657bf59c5c6
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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