Phosphorus pentachloride → HCID 10542881, compound

HRID 1169271Notes

Reaction equation

HRID 1169271 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=2)[NH:10][C:9]1=S.P(Cl)(Cl)(Cl)(Cl)[Cl:22]>O=P(Cl)(Cl)Cl>[Cl:22][C:9]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=2)[N:10]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 12088011HCID 12088011, compound

Product 1

HCID 10542881HCID 10542881, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A suspension of 306 mg (1.0 mmol) of 3-(2-chloro-phenyl)-6-fluoro-2-thioxo-2,3-dihydro-1H-quinazolin-4-one in 2.0 mL of POCl3 was treated with 350 mg of PCl5 and the mixture was refluxed for 2.5 hours. The solvent was evaporated and the residues were taken up in ethyl acetate, washed with water and brine, and then the solvent was evaporated to give 2-chloro-3-(2-chloro-phenyl)-6-fluoro-3H-quinazolin-4-one as a solid. This material was dissolved in 15 mL of absolute ethanol and 238 mg (2.20 mmol) of 2-aminomethylpyridine and the mixture was refluxed overnight. The reaction mixture was cooled and the solvent was evaporated. The residue was dissolved in ethyl acetate and washed twice with water. The organic layer was dried with brine and with MgSO4 and evaporated to give a gum which was crystallized from ether to give 190 mg (50%) of the desired product, m.p. 156-158 ° C.

Workup

  1. temperaturethe mixture was refluxed for 2.5 hours
  2. customThe solvent was evaporated
  3. washwashed with water and brine
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d64a682ad5d14666a1c5ac406f56ddb3
Source dataset
uspto-grants-2003_09
Patent number
US06627755B1

Reaction notes

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