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

HRID 349978

Reaktionsgleichung

Reaktionsgleichung von HRID 349978
[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 hours. The reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate solution was added to the residue, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated to obtain 4-chloromethyl-3-methyl-1-(2-pyridyl)-1H-pyrazole (3.10 g, yield 94%) as a colorless oily substance.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and saturated aqueous sodium bicarbonate solution
  2. additionwas added to the residue, which
  3. extractionwas extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6682ecdb3dad40cb984336166effd6f8
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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