Thionyl Chloride → 5-(Chloromethyl)-2-(1H-pyrazol-1-yl)pyridine

HRID 2075284

Reaktionsgleichung

Reaktionsgleichung von HRID 2075284
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.O=S(Cl)[Cl:16]>C(Cl)Cl>[Cl:16][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[N:11][CH:10]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 15980534(6-(1H-pyrazol-1-yl)pyridin-3-yl)methanol

Produkt 1

HCID 166559465-(Chloromethyl)-2-(1H-pyrazol-1-yl)pyridineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of alcohol (III) (10.5 g, 59.9 mmol) in CH2Cl2 (150 ml), SOCl2 (36 g, 22 ml, 299.6 mmol) was added and the resulting reaction mixture was stirred at room temperature for a period of between 12 to 18 hours. The excess SOCl2 was quenched with saturated aqueous NaHCO3. The resulting mixture was extracted with CH2Cl2 and washed with brine. Removal of solvent gave a compound of formulae (11.15 g, 95% yield) as a white solid. MS-ESI=194.06, 196.06, 1H NMR (ppm): 8.59 (H3′, d), 8.43 (H6, d), 8.03 (H2, d), 7.89 (H3, dd), 7.78 (H5′, s), 6.50 (H4′, t), 4.65 (—CH2-).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. customThe excess SOCl2 was quenched with saturated aqueous NaHCO3
  3. extractionThe resulting mixture was extracted with CH2Cl2
  4. washwashed with brine
  5. customRemoval of solvent
  6. customgave a compound of formulae (11.15 g, 95% yield) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-96a092be8c2945b8ba5f3af2f51221bb
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919627B2

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