Potassium Hydroxide → 10-(thiophen-2-ylmethyl)-2,3-dihydroimidazo[2,1-b]quinazolin-5-one

HRID 1284020Notes

Reaction equation

HRID 1284020 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:13](=O)[O:12][C:10](=O)[C:9]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:8]12.CSC1[NH:22][CH2:23][CH2:24][N:25]=1.[OH-].[K+]>O1CCOCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:8]2[C:9](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:10](=[O:12])[N:22]2[CH2:23][CH2:24][N:25]=[C:13]12

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 883692-Methylthio-2-imidazoline hydroiodideHCID 122232961-(thiophen-2-ylmethyl)-3,1-benzoxazine-2,4-dione

Product 1

HCID 1222331310-(thiophen-2-ylmethyl)-2,3-dihydroimidazo[2,1-b]quinazolin-5-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 20 g. of N-(2-thienylmethyl)isatoic anhydride, 9 g. of 2-methylmercapto-imidazoline and 1 pellet of potassium hydroxide in about 300 ml. of dioxane is heated at reflux for 5 hours, the solvent then evaporated off and the residue dissolved in methylene chloride. After washing twice with water the solution is extracted 3 times with 1N. hydrochloric solution. Heating on a steam bath avoids precipitation and after filtering hot through celite, sodium bicarbonate solution is added and the resulting precipitate is recovered by filtering, washed with water, dissolved in methylene chloride and the methylene chloride exchanged for diethyl ether. The resulting precipitate is recovered by filtering, washed with diethyl ether and dried under reduced pressure at 40°C. to obtain 10-(2-thienylmethyl)-2,3-dihydro-imidazo[2,1-b]quinazolin-5(10H)-one, m.p. 124°-127°C.

Workup

  1. additionA mixture of 20 g
  2. temperatureat reflux for 5 hours
  3. customthe solvent then evaporated off
  4. dissolutionthe residue dissolved in methylene chloride
  5. washAfter washing twice with water the solution
  6. extractionis extracted 3 times with 1N
  7. temperatureHeating on a steam bath
  8. customavoids precipitation
  9. filtrationafter filtering hot through celite, sodium bicarbonate solution
  10. additionis added
  11. customthe resulting precipitate is recovered
  12. filtrationby filtering
  13. washwashed with water
  14. dissolutiondissolved in methylene chloride
  15. customThe resulting precipitate is recovered
  16. filtrationby filtering
  17. washwashed with diethyl ether
  18. customdried under reduced pressure at 40°C.

Sources & evidence

ORD record
ord-420f01ea3e9049b8b6747116b34d2448
Source dataset
uspto-grants-1976_08
Patent number
US03978059

Reaction notes

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