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Ethanol → 4-Ethoxy-2-methylthio-6-[3-(trifluoromethyl)phenoxy]pyrimidine

HRID 801
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 801
[CH2:1]([OH:3])[CH3:2].[H-].[Na+].Cl[C:7]1[CH:12]=[C:11](Cl)[N:10]=[C:9]([S:14][CH3:15])[N:8]=1.[F:16][C:17]([F:26])([F:25])[C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1>C1COCC1.CN(C=O)C>[CH2:1]([O:3][C:7]1[CH:12]=[C:11]([O:24][C:20]2[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:25])[F:26])[CH:19]=2)[N:10]=[C:9]([S:14][CH3:15])[N:8]=1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydride2×HCID 805314,6-Dichloro-2-(methylthio)pyrimidine

Produkt 1

HCID 196938684-Ethoxy-2-methylthio-6-[3-(trifluoromethyl)phenoxy]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ethanol (1.18 g, 0.0256×1.0 mol) and NaH (1.02 g, (ca.60% in mineral oil), 0.0256×1.0 mol) were dissolved in THF and 4,6-dichloro-2-methylthiopyrimidine (Compound No. VII-23)(5.0 g, 0.0256 mol) was added thereto. The resulting solution was stirred for about 30 minutes at room temperature. To this reaction solution, m-trifluoromethyl-phenol (6.23 g, 0.0256×1.5 mol), NaH (1.54 g, (ca.60% in mineral oil), 0.0256×1.5 mol), and KI (2.12 g, 0.0256×0.5 mol) dissolved in DMF were added. The resulting solution was refluxed for about 7 hours. The reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate to separate an organic phase. The organic phase was washed with aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and concentrated, and thereafter purified on a silica gel column.

Aufarbeitung

  1. additionVII-23)(5.0 g, 0.0256 mol) was added
  2. additionwere added
  3. temperatureThe resulting solution was refluxed for about 7 hours
  4. customThe reaction solution was partitioned between ethyl acetate and aqueous saturated sodium hydrogen carbonate
  5. customto separate an organic phase
  6. washThe organic phase was washed with aqueous saturated sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-0c41a886f892437a80e1ebfc69bc8999
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05723412

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