Methanol → (+/-)-2-[3-chloro-4-[(4-chlorophenyl)[(1H-imidazol-2-ylmethyl)amino]methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione

HRID 984048Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 984048
CO.[Na].[NH:4]1[CH:8]=[CH:7][N:6]=[C:5]1[CH2:9][NH2:10].[Cl:11][C:12]1[CH:13]=[C:14]([N:27]2[C:32](=[O:33])[NH:31][C:30](=[O:34])[CH:29]=[N:28]2)[CH:15]=[CH:16][C:17]=1[CH:18](Cl)[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1>C(#N)C>[Cl:11][C:12]1[CH:13]=[C:14]([N:27]2[C:32](=[O:33])[NH:31][C:30](=[O:34])[CH:29]=[N:28]2)[CH:15]=[CH:16][C:17]=1[CH:18]([C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[NH:10][CH2:9][C:5]1[NH:4][CH:8]=[CH:7][N:6]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 13820412-aminomethyl-1H-imidazoleHCID 5360545SodiumHCID 225573573-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl-1,2,4-triazine-3,5(2H,4H)-dione

Produkt 1

HCID 22557371(+/-)-2-[3-chloro-4-[(4-chlorophenyl)[(1H-imidazol-2-ylmethyl)amino]methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dioneAusbeute 16,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Methanol (100 ml) was stirred at RT and sodium (0.09 mol) was added. The mixture was stirred until complete dissolution. (1H-imidazol-2-yl)methanamine (0.045 mol) was added. The mixture was stirred for 30 minutes. NaCl was removed by filtration and the filtrate was evaporated. Toluene was added and azeotroped on the rotary evaporator. 2-[3-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.015 mol) and acetonitrile (50 ml) were added. The resulting reaction mixture was stirred and refluxed for 20 hours. The solvent was evaporated, the residue was stirred in water, and extracted with CH2Cl2/CH3OH (90/10). The separated organic layer was dried, filtered, and the solvent evaporated. The residue was purified over silica gel on a glass filter (eluent: CH2Cl2/CH3OH 90/10). The pure fractions were collected and the solvent was evaporated. The residue was stirred in CH3CN, filtered off, washed with DIPE, then dried, yielding 1.1 g (16.5%) of (±)-2-[3-chloro-4-[(4-chlorophenyl)[(1H-imidazol-2-ylmethyl)amino]methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (compound 50).

Aufarbeitung

  1. stirringThe mixture was stirred for 30 minutes
  2. customNaCl was removed by filtration
  3. customthe filtrate was evaporated
  4. additionToluene was added
  5. customazeotroped on the rotary evaporator
  6. customThe resulting reaction mixture
  7. stirringwas stirred
  8. temperaturerefluxed for 20 hours
  9. customThe solvent was evaporated
  10. stirringthe residue was stirred in water
  11. extractionextracted with CH2Cl2/CH3OH (90/10)
  12. customThe separated organic layer was dried
  13. filtrationfiltered
  14. customthe solvent evaporated
  15. customThe residue was purified over silica gel on a glass
  16. filtrationfilter (eluent: CH2Cl2/CH3OH 90/10)
  17. customThe pure fractions were collected
  18. customthe solvent was evaporated
  19. stirringThe residue was stirred in CH3CN
  20. filtrationfiltered off
  21. washwashed with DIPE
  22. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8c82806b5d3d4ce68304f999c8143434
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867207B2

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