Thionyl Chloride → 2-[4-(Chloromethyl)-3-methyl-1H-pyrazol-1-YL]pyridine

HRID 1294192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1294192
[CH3:1][C:2]1[C:6]([CH2:7]O)=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1.S(Cl)([Cl:17])=O>C1(C)C=CC=CC=1>[Cl:17][CH2:7][C:6]1[C:2]([CH3:1])=[N:3][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 23076503[3-Methyl-1-(pyridin-2-yl)-1H-pyrazol-4-yl]methanol

Produkt 1

HCID 178612892-[4-(Chloromethyl)-3-methyl-1H-pyrazol-1-YL]pyridineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 3-methyl-1-(2-pyridyl)-1H-pyrazol-4-ylmethanol (3.00 g), thionyl chloride (2.5 mL) and toluene (50 mL) was stirred at 70° C. for 2 hrs. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate was added to the residue. The mixture was extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 4-chloromethyl-3-methyl-1-(2-pyridyl)-1H-pyrazole (3.10 g, yield 94%) as a colorless oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium hydrogencarbonate
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ea7d6ce1baf2443bab12727811e12c75
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238716B2

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