Acetonitrile → HCID 21438854, compound

HRID 329162Notes

Reaction equation

HRID 329162 reaction equation
CC(C[N:5]1[C:11](=[O:12])O[C:8](=O)[C:7]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:6]12)=O.CS[C:19](=[NH:22])NC.I.[CH3:24]N(C)C(=N)S.C(=O)([O-])[O-].[Na+].[Na+].[C:36](#[N:38])[CH3:37]>>[CH3:37][C:36]1[CH:19]([CH3:24])[N:22]2[C:11](=[O:12])[N:5]=[C:6]3[C:7]([CH:13]=[CH:14][CH:15]=[CH:16]3)=[C:8]2[N:38]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 1222600357384-79-9HCID 178484400HCID 178484400, compound

Product 1

HCID 21438854HCID 21438854, compound

Procedure

A mixture of 11.0 g. of N-methylcarbonylmethyl isatoic anhydride, 16.6 g. of S,N-dimethyl-thiopseudourea -dimethyl-thiopseudourea hydroiodide, 5.5 g. of sodium carbonate and 150 ml. of acetonitrile is refluxed for one-half hour, filtered, evaporated to dryness, the residue dissolved in methylene chloride and evaporated again to dryness. The residue is taken up in diglyme, refluxed for one-half hour and cooled with stirring to obtain a precipitate which is recovered by filtering, washed with ether, dissolved in methylene chloride, treated with carbon, alumina and sodium sulfate, filtered through celite, and the methylene chloride exchanged for ether. The resulting precipitate is recovered by filtering, washed with ether and dried under reduced pressure to obtain 2,3-dimethyl-imidazo[1,2-c]quinazolin-5(3H)-one, m.p. 234°-237° C.

Workup

  1. additionA mixture of 11.0 g
  2. filtrationfiltered
  3. customevaporated to dryness
  4. dissolutionthe residue dissolved in methylene chloride
  5. customevaporated again to dryness
  6. temperaturerefluxed for one-half hour
  7. temperaturecooled
  8. customto obtain a precipitate which
  9. customis recovered
  10. filtrationby filtering
  11. washwashed with ether
  12. dissolutiondissolved in methylene chloride
  13. additiontreated with carbon, alumina and sodium sulfate
  14. filtrationfiltered through celite
  15. customThe resulting precipitate is recovered
  16. filtrationby filtering
  17. washwashed with ether
  18. customdried under reduced pressure

Sources & evidence

ORD record
ord-02cc006ac98942f2ad1d2d9652b4a004
Source dataset
uspto-grants-1977_04
Patent number
US04020062

Reaction notes

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