Dimethylformamide → 2-(1-Methylpropyl)-3H-1,2,4-triazole-3-one

HRID 1699348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1699348
OC1C=CC(N2CCN(C3C=CC([N:20]4[CH:24]=[N:23][N:22]([C@@H:25]([CH3:28])[CH2:26][CH3:27])[C:21]4=[O:29])=CC=3)CC2)=CC=1.[OH-].[Na+].CN(C)C=O>O>[CH3:28][CH:25]([N:22]1[C:21](=[O:29])[NH:20][CH:24]=[N:23]1)[CH2:26][CH3:27]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 9918902,4-Dihydro-4-(4-(4-(4-hydroxyphenyl)-1-piperazinyl)phenyl)-2-((1S)-1-methylpropyl)-3H-1,2,4-triazol-3-one2×

Produkt 1

HCID 1357235282-(1-Methylpropyl)-3H-1,2,4-triazole-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 6.7 g of (+)-(2R,cis)-2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl-methyl)-1,3-dioxolane-4-methanol 4-methylbenzenesulfonate(ester) 4-methyl-benzenesulfonate(salt 1:1) (intermediate (10)), 3.9 g of (+)-(S)-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one (intermediate (7)), 1.5 g of sodium hydroxide flakes and 100 ml of N,N-dimethylformamide was stirred overnight at 50° C. under a nitrogen atmosphere. After cooling, water was added to the reaction mixture. The precipitate was filtered off and taken up in dichloromethane. The organic layer was dried, filtered and evaporated. The residue was triturated with methanol, yielding 5.6 g (83.2%) of (+)-[2R-[2α,4α,4(S)]]-4-[4-[4-[[2-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one; mp. 182.4° C.; [α]D20=+14.130° (c=1% in methanol) (comp. 8).

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered off
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was triturated with methanol

Quellen und Nachweise

ORD-Eintrag
ord-3c1eecfadb5544d0b8999c27a7a5462d
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06346518B1

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