Sodium Hydroxide → 10-(4-Fluorophenyl)-2,10-dihydroimidazo[2,1-b]quinazolin-5(3H)-one

HRID 918197Notes

Reaction equation

HRID 918197 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=O)[O:13][C:11](=O)[C:10]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:9]23)=[CH:4][CH:3]=1.CSC1[NH:23][CH2:24][CH2:25][N:26]=1.[OH-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:9]3[C:10](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:11](=[O:13])[N:23]3[CH2:24][CH2:25][N:26]=[C:14]23)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 883692-Methylthio-2-imidazoline hydroiodideHCID 12226008HCID 12226008, compound

Product 1

HCID 306383910-(4-Fluorophenyl)-2,10-dihydroimidazo[2,1-b]quinazolin-5(3H)-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5.4 g. of N-(p-fluoro-phenyl)isatoic anhydride, 2.5 g. of 2-methylmercapto-imidazoline and one pellet (about 100 mg.) sodium hydroxide in 75 ml. of dioxane is refluxed with stirring for 4 hours. The resulting mixture is evaporated to dryness, the residue dissolved in methylene chloride, washed with water and extracted twice with 1N hydrochloric acid. The combined aqueous extracts are washed with methylene chloride and then with diethyl ether and made basic with sodium bicarbonate. The resulting precipitate is filtered off, washed thoroughly with water, dried by suction, dissolved in methylene chloride, dried with sodium sulfate, treated with charcoal and the methylene chloride exchanged for methanol to crystallize 10-(p-fluoro-phenyl)-2,3-dihydro-imidazo[2,1-b]quinazolin-5(10H)-one, m.p. 278°-280°C.

Workup

  1. customThe resulting mixture is evaporated to dryness
  2. dissolutionthe residue dissolved in methylene chloride
  3. washwashed with water
  4. extractionextracted twice with 1N hydrochloric acid
  5. washThe combined aqueous extracts are washed with methylene chloride
  6. filtrationThe resulting precipitate is filtered off
  7. washwashed thoroughly with water
  8. customdried by suction
  9. dissolutiondissolved in methylene chloride
  10. dry with materialdried with sodium sulfate
  11. additiontreated with charcoal
  12. customto crystallize 10-(p-fluoro-phenyl)-2,3-dihydro-imidazo[2,1-b]quinazolin-5(10H)-one, m.p. 278°-280°C.

Sources & evidence

ORD record
ord-e6524af921ba466e8234585c63884b08
Source dataset
uspto-grants-1976_07
Patent number
US03969506

Reaction notes

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