Phosphorus oxychloride → HCID 22030371, compound

HRID 968557Notes

Reaction equation

HRID 968557 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1.O=P(Cl)(Cl)[Cl:24]>>[Cl:24][C:13]1[C:12]2[C:17](=[CH:18][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:2]([F:21])([F:20])[F:1])=[CH:10][CH:11]=2)[N:16]=[CH:15][N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135682057HCID 135682057, compound

Product 1

HCID 22030371HCID 22030371, compound

Procedure

Reflux a solution of 7-(2-Trifluoromethyl-phenyl)-3H-quinazolin-4-one (1.12 g, 0.0039 mol) in POCl3 for 16 hours. Cool the mixture and concentrate under reduced pressure. Partition the residue between saturated aqueous NaHCO3 and EtOAc. Wash the EtOAc layer once with additional NaHCO3, dry it (Na2SO4), and concentrate under reduced pressure to obtain the crude product as a solid. Filter the residue through a 2 inch pad of silica gel (50% EtOAc/Hexanes) and concentrate under reduce pressure to give 4-chloro-7-(2-trifluoromethyl-phenyl)-quinazoline as a pale yellow-brown solid.

Workup

  1. temperatureCool the mixture
  2. concentrationconcentrate under reduced pressure
  3. customPartition the residue between saturated aqueous NaHCO3 and EtOAc
  4. washWash the EtOAc layer once with additional NaHCO3
  5. dry with materialdry it (Na2SO4)
  6. concentrationconcentrate under reduced pressure
  7. customto obtain the crude product as a solid
  8. filtrationFilter the residue through a 2 inch pad of silica gel (50% EtOAc/Hexanes)
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-1d64491f55594bbab1e8e28ff5e81d09
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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