Phosphorus pentachloride → HCID 10542881, compound

HRID 1169270Notes

Reaction equation

HRID 1169270 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 265 mg (0.87 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 300 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 10 mL of absolute ethanol and 216 mg (1.73 mmol) of 2-fluorobenzylamine and the mixture was refluxed overnight. The reaction mixture was cooled and the solvent was evaporated. The residues were partitioned between ethyl acetate and dilute HCl and the aqueous phase was extracted further with ethyl acetate. The combined organic extracts were dried with brine and with magnesium sulfate (MgSO4) and evaporated to give a gum which was crystallized from ether to give 157 mg (45%) of the desired product, m.p. 163-165° 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-13a9ddaa214342c9b39f31d72472a39c
Source dataset
uspto-grants-2003_09
Patent number
US06627755B1

Reaction notes

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