Sodium Hydroxide → 10-cyclopropylmethyl-2,3-dihydroimidazo[2,1-b]quinazolin-5(10H)-one hydrogen maleate

HRID 918195Notes

Reaction equation

HRID 918195 reaction equation
I.CS[C:4]1[NH:5][CH2:6][CH2:7][N:8]=1.[CH:9]1([CH2:12][N:13]2C(=O)[O:18][C:16](=[O:17])[C:15]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:14]23)[CH2:11][CH2:10]1.[OH-:25].[Na+].[O:27]1[CH2:32][CH2:31]OCC1>>[C:16]([OH:18])(=[O:17])/[CH:15]=[CH:31]\[C:32]([OH:27])=[O:25].[CH:9]1([CH2:12][N:13]2[C:14]3[C:15](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:16](=[O:17])[N:5]3[CH2:6][CH2:7][N:8]=[C:4]23)[CH2:11][CH2:10]1

Participants

5

Reactant 4

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 11672969N-(cyclopropylmethyl)isatoic anhydrideHCID 122212281H-Imidazole, 4,5-dihydro-2-(methylthio)-, hydriodide (1:1)

Product 1

HCID 6814044910-cyclopropylmethyl-2,3-dihydroimidazo[2,1-b]quinazolin-5(10H)-one hydrogen maleate

Conditions

Temperature
20 °C

Procedure

A charge of 100 ml. of dioxane, 3.5 g. 2-methylmercaptoimidazoline hydroiodide, 6 g. N-(cyclopropylmethyl)isatoic anhydride and 2 pellets of sodium hydroxide is refluxed for 1 hour in a reaction vessel. The reaction is cooled to 20°C. and the solvent evaporated. The residue is dissolved in methylene chloride and this solution is extracted with 1 normal hydrochloride solution. The acid solution is extracted with methylene chloride (discard) and with ether (discard) and then made basic with 10% sodium bicarbonate solution. The precipitate which forms is filtered off, washed with water and dissolved in methylene chloride. After drying with anhydrous sodium sulfate, the solvent is exchanged from ether and the product crystallized by additon of pentane. This material is converted into its hydrogen maleate addition salt by conventional procedures to obtain 10-cyclopropylmethyl-2,3-dihydroimidazo[2,1-b]quinazolin-5(10H)-one hydrogen maleate, m.p. 189°-192°C.

Workup

  1. additionA charge of 100 ml
  2. customthe solvent evaporated
  3. dissolutionThe residue is dissolved in methylene chloride
  4. extractionthis solution is extracted with 1 normal hydrochloride solution
  5. extractionThe acid solution is extracted with methylene chloride (discard) and with ether (discard)
  6. filtrationThe precipitate which forms is filtered off
  7. washwashed with water
  8. dissolutiondissolved in methylene chloride
  9. dry with materialAfter drying with anhydrous sodium sulfate
  10. customthe product crystallized by additon of pentane
  11. additionThis material is converted into its hydrogen maleate addition salt by conventional procedures

Sources & evidence

ORD record
ord-1eb98410193e4b78b01ff8d1c29ec929
Source dataset
uspto-grants-1976_07
Patent number
US03969506

Reaction notes

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