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2,2,2-Trifluoroethanol → HCID 68108403, Verbindung

HRID 1752480
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1752480
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:13][O:14][C:15]([C:17]1[C:22]([NH2:23])=[N:21][C:20](Cl)=[CH:19][N:18]=1)=[O:16].[NH4+].[Cl-]>>[CH3:13][O:14][C:15]([C:17]1[C:22]([NH2:23])=[N:21][C:20]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[CH:19][N:18]=1)=[O:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 64092,2,2-TrifluoroethanolHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 53417426Methyl 3-amino-5-chloropyrazine-2-carboxylate

Produkt 1

HCID 68108403HCID 68108403, Verbindung

Versuchsvorschrift

A mixture of 2,2,2-trifluoro-ethanol (6.9 ml, 96 mmol) and cesium carbonate (1.56 g, 4.8 mmol) was stirred for 20 min, 3-amino-5-chloro-pyrazine-2-carboxylic acid methyl ester [28643-16-5] (600 mg, 3.2 mmol) was added and the mixture was stirred at rt for 42 h. To complete the reaction the mixture was heated to reflux for another 3 h. Saturated aq. NH4Cl was added and the mixture was extracted with EtOAc, the combined organic layers were washed with saturated aq. sodium chloride, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 3:7) to provide the title compound as colorless solid.

Aufarbeitung

  1. stirringthe mixture was stirred at rt for 42 h
  2. customthe reaction the mixture
  3. temperaturewas heated
  4. temperatureto reflux for another 3 h
  5. extractionthe mixture was extracted with EtOAc
  6. washthe combined organic layers were washed with saturated aq. sodium chloride
  7. dry with materialdried with Na2SO4
  8. customevaporated
  9. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 3:7)

Quellen und Nachweise

ORD-Eintrag
ord-7100da3fa84e4b8b99a86e3a5a4a9be3
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09163011B2

Notizen zur Reaktion

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