Formamide → (+/-)-N-[[2-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4 triazin-2(3H)-yl)phenyl](4-chlorophenyl)methyl]formamide

HRID 984038Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 984038
[Cl:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[CH:19]=[N:18]2)[CH:5]=[CH:6][C:7]=1[C:8](=O)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1.O.[CH:26]([NH2:28])=[O:27]>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[NH:21][C:20](=[O:24])[CH:19]=[N:18]2)[CH:5]=[CH:6][C:7]=1[CH:8]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[NH:28][CH:26]=[O:27]

Komponenten

5

Edukt 3

HCID 713FormamideHCID 962WaterHCID 161969CP 25415

Produkt 1

HCID 22557358(+/-)-N-[[2-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4 triazin-2(3H)-yl)phenyl](4-chlorophenyl)methyl]formamideAusbeute 22,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 2-[3-chloro-4-(4-chlorobenzoyl)phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.081 mol) in formic acid (120 ml) and formamide (300 ml) was stirred for 16 hours at 160° C. The reaction mixture was cooled, poured out into water (600 ml) and the resulting precipitate was filtered off and dried. This fraction was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated. The residue was stirred in DIPE, filtered off, and dried, yielding 8.78 g (22.5%) of (±)-N-[[2-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)phenyl](4-chlorophenyl)methyl]formamide (interm. 64).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe resulting precipitate was filtered off
  3. customdried
  4. customThis fraction was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  5. customThe pure fractions were collected
  6. customthe solvent was evaporated
  7. stirringThe residue was stirred in DIPE
  8. filtrationfiltered off
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-58f9f2c91e4048e1af993c2c5697466e
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867207B2

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