Potassium Hydroxide → HCID 21433254, compound

HRID 2398536Notes

Reaction equation

HRID 2398536 reaction equation
[C:1]([O:4][CH2:5][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)(=[O:3])[CH3:2].CSC1[NH:22][CH2:23][CH2:24][N:25]=1.[OH-].[K+]>O1CCOCC1>[C:1]([O:4][CH2:5][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)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 883692-Methylthio-2-imidazoline hydroiodideHCID 122260002-(2,4-dioxo-3,1-benzoxazin-1-yl)ethyl acetate

Product 1

HCID 21433254HCID 21433254, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 18 g. of N-(2-acetoxyethyl)isatoic anhydride, 8.5 g. of 2-methylmercapto-imidazoline and 2 pellets of potassium hydroxide in 300 ml. of dioxane is heated at reflux for 5 hours, the solvent then evaporated off and water added. The resulting precipitate is recovered by filtering and washed twice with water. The precipitate is dissolved in methylene chloride and extracted 3times with 1N. hydrochloric solution. The combined hydrochloric acid solutions and filtered through celite, sodium carbonate solution is added and the resulting precipitate is recovered by filtering, washed with water, air dried, dissolved in methylene chloride, dried, filtered and the methylene chloride exchanged for diethyl ether. The resulting precipitate is recovered by filtering, washed with cold diethyl ether and dried under reduced pressure at 40° C. to obtain 10-(2'-acetoxyethyl)-2,3-dihydro-imidazo[2,1-b] quinazolin-5(10H)-one, m.p. 124°-126° C.

Workup

  1. additionA mixture of 18 g
  2. temperatureat reflux for 5 hours
  3. customthe solvent then evaporated off
  4. additionwater added
  5. customThe resulting precipitate is recovered
  6. filtrationby filtering
  7. washwashed twice with water
  8. dissolutionThe precipitate is dissolved in methylene chloride
  9. extractionextracted 3times with 1N
  10. filtrationThe combined hydrochloric acid solutions and filtered through celite, sodium carbonate solution
  11. additionis added
  12. customthe resulting precipitate is recovered
  13. filtrationby filtering
  14. washwashed with water, air
  15. customdried
  16. dissolutiondissolved in methylene chloride
  17. customdried
  18. filtrationfiltered
  19. customThe resulting precipitate is recovered
  20. filtrationby filtering
  21. washwashed with cold diethyl ether
  22. customdried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-a8ee9f31ec244117b5d532a2a1e49cca
Source dataset
uspto-grants-1977_05
Patent number
US04025511

Reaction notes

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