Thionyl Chloride → 4-Chloro-7-fluoro-6-nitroquinazoline

HRID 1968650Notes

Reaction equation

HRID 1968650 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].S(Cl)([Cl:18])=O>CN(C=O)C>[Cl:18][C:6]1[C:5]2[C:10](=[CH:11][C:2]([F:1])=[C:3]([N+:13]([O-:15])=[O:14])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178526403HCID 178526403, compound

Product 1

HCID 106093584-Chloro-7-fluoro-6-nitroquinazoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

7-Fluoro-6-nitroquinazolin-4-ol (518 mg, 2 mmol) was dissolved into thionyl chloride (3 mL) containing 2 drops of DMF. The solution was refluxed for 3 h. The solvent was removed under reduced pressure to afford 4-chloro-7-fluoro-6-nitroquinazoline, which was used directly in the next step without purification.

Workup

  1. temperatureThe solution was refluxed for 3 h
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0c71aba21f6c4b4f9d55df9baae9515b
Source dataset
uspto-grants-2013_04
Patent number
US08426430B2

Reaction notes

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