Thionyl Chloride → 4-Chloro-7-nitroquinazoline

HRID 1968633Notes

Reaction equation

HRID 1968633 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8](O)=[N:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:17])=O>CN(C=O)C>[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 178526462HCID 178526462, compound

Product 1

HCID 8306804-Chloro-7-nitroquinazolineYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-nitroquinazolin-4-ol (3.4 g, 17.79 mmol), thionyl chloride (20 mL), and DMF (0.5 mL) was refluxed for 48 h. After the mixture was cooled, excess thionyl chloride was removed by evaporation and the residue was azeotroped with toluene to afford 2.61 g (70%) of 4-chloro-7-nitroquinazoline as a yellowish solid.

Workup

  1. temperaturewas refluxed for 48 h
  2. temperatureAfter the mixture was cooled
  3. customexcess thionyl chloride was removed by evaporation
  4. customthe residue was azeotroped with toluene

Sources & evidence

ORD record
ord-fad8eed217c440ae93cef1ffebf094be
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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