1,4-Dioxane → Fluquazone

HRID 1395150Notes

Reaction equation

HRID 1395150 reaction equation
[F:1][C:2]([F:23])([F:22])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:6][C:5]1=S.[O:24]1CCOCC1.[K]>C(O)=O.O>[F:1][C:2]([F:23])([F:22])[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:6][C:5]1=[O:24]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 5462222PotassiumHCID 203406541-(2,2,2-trifluoroethyl)-4-phenyl-6-chloro-3,4-dihydro-2(1H)-quinazolinethione

Product 1

HCID 219069Fluquazone

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 962WaterSolvent

Procedure

To a solution of 1.5 g of 1-(2,2,2-trifluoroethyl)-4-phenyl-6-chloro-3,4-dihydro-2(1H)-quinazolinethione in 50 ml. of dioxane was added dropwise a solution of 3 g of potassium permangenate in 20 ml. of water. The mixture was stirred at room temperature for 2 hours and then a few drops of formic acid was added. The resultant brown precipitate was filtered off and washed with chloroform. The filtrate was concentrated under reduced pressure and the residue was dissolved in 30 ml. of chloroform. The chloroform solution was combined, washed successively with dilute sodium hydroxide solution and water, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was recrystallized from isopropyl alcohol to give 1 g of 1-(2,2,2-trifluoroethyl)-4-phenyl-6-chloro-2(1H)-quinazolinone, m.p. 184.0°-185.0° C.

Workup

  1. filtrationThe resultant brown precipitate was filtered off
  2. washwashed with chloroform
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in 30 ml
  5. washwashed successively with dilute sodium hydroxide solution and water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-1804be5b322e4790a48a11bd6a4dc91e
Source dataset
uspto-grants-1980_05
Patent number
US04202895

Reaction notes

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