Acetonitrile → HCID 21535595, compound

HRID 1076974Notes

Reaction equation

HRID 1076974 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:13](=O)[O:12][C:10](=O)[C:9]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:8]23)=[CH:4][CH:3]=1.I.CSC(=N)[NH:25][CH2:26][CH:27]=[CH2:28].C(=O)([O-])[O-].[Na+].[Na+].C(#[N:38])C>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:8]3[C:9](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:10](=[O:12])[N:38]=[C:13]2[NH:25][CH2:26][CH:27]=[CH2:28])=[CH:19][CH:20]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 12223278N-(p-fluorobenzyl)isatoic anhydrideHCID 178457615HCID 178457615, compound

Product 1

HCID 21535595HCID 21535595, compound

Procedure

A suspension of 13.5 g. of N-(4'-fluorobenzyl)isatoic anhydride, 130 g. of S-methyl-N-allylthiopseudourea hydroiodide and 75 g. of powdered sodium carbonate in 500 ml. of acetonitrile is heated with stirring at reflux for 1.5 hours. The excess sodium carbonate is filtered off and the solvent evaporated to dryness. The residue is dissolved in methylene chloride, filtered to remove insolubles and the filtrate evaporated to dryness. The residue is dissolved in 500 ml. of diglyme and the resulting solution heated at reflux for 1.5 hours. After cooling, methylene chloride is added to obtain a precipitate which is recovered by filtering, washed twice with methylene chloride and once with ether, dried, dissolved in methanol, filtered and concentrated on a steam bath to obtain a precipitate which is recovered by filtering, washed with methanol and dried under reduced pressure to obtain 1-(4'-fluorobenzyl)-2-allylamino-quinazolin-4(1H)-one, m.p. 155°-157°C. (additional quantities of the title compound are recovered from the mother liquid).

Workup

  1. additionA suspension of 13.5 g
  2. temperatureat reflux for 1.5 hours
  3. filtrationThe excess sodium carbonate is filtered off
  4. customthe solvent evaporated to dryness
  5. dissolutionThe residue is dissolved in methylene chloride
  6. filtrationfiltered
  7. customto remove insolubles
  8. customthe filtrate evaporated to dryness
  9. dissolutionThe residue is dissolved in 500 ml
  10. temperatureof diglyme and the resulting solution heated
  11. temperatureat reflux for 1.5 hours
  12. temperatureAfter cooling
  13. additionmethylene chloride is added
  14. customto obtain a precipitate which
  15. customis recovered
  16. filtrationby filtering
  17. washwashed twice with methylene chloride and once with ether
  18. customdried
  19. dissolutiondissolved in methanol
  20. filtrationfiltered
  21. concentrationconcentrated on a steam bath
  22. customto obtain a precipitate which
  23. customis recovered
  24. filtrationby filtering
  25. washwashed with methanol
  26. customdried under reduced pressure

Sources & evidence

ORD record
ord-4a98e23e111a4ccba31ae5684edee916
Source dataset
uspto-grants-1976_05
Patent number
US03959279

Reaction notes

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