Water → HCID 16756984, Verbindung

HRID 1963013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963013
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH2:13]O)[S:10][N:9]=2)=[CH:4][CH:3]=1.P(Br)(Br)[Br:16].O>C1(C)C=CC=CC=1>[Br:16][CH2:13][C:11]1[S:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:12]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 16756661HCID 16756661, Verbindung

Produkt 1

HCID 16756984HCID 16756984, VerbindungAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of [3-(4-chlorophenyl)-[1,2,4]thiadiazol-5-yl]-methanol (0.25 g, 1.10 mmol) in toluene (8 ml) was added PBr3 (0.17 ml, 1.65 mmol). The resulting reaction mixture was refluxed at 120° C. for 15 min. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to 0° C., added water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organics was washed with saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 2% EtOAc-Hexane) to get the desired product (0.24 g, 75%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. temperaturethe reaction mixture was cooled to 0° C.
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washThe combined organics was washed with saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude residue was purified over silica gel (100-200 M, 2% EtOAc-Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-654b535c1deb4af1940fa6902bbcfe54
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415383B2

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