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

HRID 1051117Notes

Reaction equation

HRID 1051117 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].O=S(Cl)[Cl:18]>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-nitroquinazolineYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

7-fluoro-6-nitroquinazolin-4-ol (15 g, 0.072 mol) was added to 150 ml SOCl2 and 10 drops of DMF was added. The solution was heated to reflux for 4 hours which become a clear solution, then the SOCl2 was removed under reduce pressure to give 4-chloro-7-fluoro-6-nitroquinazoline as yellow powder 15.4 g (94.4% yield).

Workup

  1. additionwas added
  2. temperatureThe solution was heated
  3. temperatureto reflux for 4 hours which
  4. customthe SOCl2 was removed

Sources & evidence

ORD record
ord-bf17cc17249648a7a2825e5ddf7d6505
Source dataset
uspto-grants-2016_07
Patent number
US09388160B2

Reaction notes

Loading…