Phosphorus oxychloride → HCID 86667782, compound

HRID 2400265Notes

Reaction equation

HRID 2400265 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:17][C:16](=O)[C:15]3[C:10](=[CH:11][C:12]([C:19]([F:22])([F:21])[F:20])=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:25])=O>O1CCOCC1>[Cl:25][C:16]1[C:15]2[C:10](=[CH:11][C:12]([C:19]([F:22])([F:21])[F:20])=[CH:13][CH:14]=2)[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:17]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136332414HCID 136332414, compound

Product 1

HCID 86667782HCID 86667782, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred suspension of 2-(4-chlorophenyl)-7-trifluoromethyl-3H-quinazolin-4-one (50 g, 0.15 mol) in dioxane (400 mL) was added dropwise phosphorus oxychloride (43 mL, 0.46 mol). The suspension was then heated at reflux for 2 h then allowed to cool to room temperature and evaporated under reduced pressure. The remaining solid was dissolved in dioxane (1 L) and an aqueous solution of sodium hydroxide (50 mL, 10% weight/weight (w/w)) was added dropwise maintaining the internal temperature≦10° C.). Water (1 L) was then added to the resultant suspension followed by the dropwise addition of a further quantity of aqueous sodium hydroxide (90 mL, 10% w/w). The precipitate was isolated by vacuum filtration washing with water (3×500 mL) and dried under vacuum (10 mbar, 50° C.). Yield=49 g, 93%; LC-MS: 4.7 min, 343 (M+); 1H NMR (dimethylsulfoxide (DMSO)-d6) δ 7.68 (d, 2 H, J=8.9 Hz), 8.12 (dd, 1 H, J=8.9, 1.8 Hz), 8.48-8.54 (m, 4 H).

Workup

  1. temperatureThe suspension was then heated
  2. temperatureat reflux for 2 h
  3. customevaporated under reduced pressure
  4. dissolutionThe remaining solid was dissolved in dioxane (1 L)
  5. additionan aqueous solution of sodium hydroxide (50 mL, 10% weight/weight (w/w)) was added dropwise
  6. temperaturemaintaining the internal temperature≦10° C.)
  7. additionWater (1 L) was then added to the resultant suspension
  8. additionfollowed by the dropwise addition of a further quantity of aqueous sodium hydroxide (90 mL, 10% w/w)
  9. customThe precipitate was isolated by vacuum filtration
  10. washwashing with water (3×500 mL)
  11. customdried under vacuum (10 mbar, 50° C.)
  12. custom4.7 min, 343 (M+)

Sources & evidence

ORD record
ord-7ccae8a08107465690ee6f847f09517a
Source dataset
uspto-grants-2014_08
Patent number
US08796180B2

Reaction notes

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