Sodium Hydroxide → 10-Benzyl-2,3-dihydroimidazo(2,1-B)quinazolin-5(10H)-one

HRID 918188

Reaction equation

HRID 918188 reaction equation
[CH2:1]([N:8]1[C:14](=O)[O:13][C:11](=O)[C:10]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:9]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CSC1[NH:23][CH2:24][CH2:25][N:26]=1.[OH-].[Na+]>O1CCOCC1>[CH2:1]([N:8]1[C:9]2[C:10](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:11](=[O:13])[N:23]2[CH2:24][CH2:25][N:26]=[C:14]12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 883692-Methylthio-2-imidazoline hydroiodideHCID 520756N-Benzylisatoic anhydride

Product 1

HCID 413451510-Benzyl-2,3-dihydroimidazo(2,1-B)quinazolin-5(10H)-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 12.7 g. of N-benzylisatoic anhydride, 5.8 g. of 2-methylmercapto-imidazoline and 2 pellets of sodium hydroxide in 200 ml. of dioxane was refluxed for 2 hours. While still hot, the mixture was then filtered through Celite and the filtrate concentrated to about 50 ml. volume. 50 ml. of diethyl ether was added and the crystalline precipitate removed by filtration. The residue was dissolved in methylene chloride, treated with charcoal, filtered through alumina, and the filtrate evaporated. The residue was crystallized from methylene chloride/diethyl ether to obtain the heading compound, m.p. 203°-205°C.

Workup

  1. additionA mixture of 12.7 g
  2. filtrationWhile still hot, the mixture was then filtered through Celite
  3. concentrationthe filtrate concentrated to about 50 ml
  4. additionof diethyl ether was added
  5. customthe crystalline precipitate removed by filtration
  6. dissolutionThe residue was dissolved in methylene chloride
  7. additiontreated with charcoal
  8. filtrationfiltered through alumina
  9. customthe filtrate evaporated
  10. customThe residue was crystallized from methylene chloride/diethyl ether
  11. customto obtain the heading compound, m.p. 203°-205°C.

Sources & evidence

ORD record
ord-13f84b6891f14562918c92aaa3ad36b8
Source dataset
uspto-grants-1976_07
Patent number
US03969506

Linked notes

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