Dimethylformamide → 3-Chloromethyl-5-(4-trifluoromethyl-phenyl)-pyridine

HRID 33522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33522
S(Cl)([Cl:3])=O.CN(C)C=O.[F:10][C:11]([F:27])([F:26])[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[C:20]([CH2:24]O)[CH:21]=[N:22][CH:23]=2)=[CH:14][CH:13]=1>ClCCl>[Cl:3][CH2:24][C:20]1[CH:21]=[N:22][CH:23]=[C:18]([C:15]2[CH:16]=[CH:17][C:12]([C:11]([F:27])([F:26])[F:10])=[CH:13][CH:14]=2)[CH:19]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1519486(5-(4-(Trifluoromethyl)phenyl)pyridin-3-yl)methanol

Produkt 1

HCID 691060983-Chloromethyl-5-(4-trifluoromethyl-phenyl)-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

177 mg (0.11 ml, 1.49 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.1 ml N,N-dimethylformamide (DMF) and 196 mg (0.74 mmol) [5-(4-Trifluoromethyl-phenyl)-pyridin-3-yl]-methanol in 6 ml dichloromethane and stirred for 1.5 h at 0° C. The mixture was poured on ice/sodium bicarbonate solution and the organic phase separated. The water phase is extracted with dichloromethane. The combined organic phases were washed with water, dried (sodium sulphate), evaporated and the obtained material (174 mg, 81%) used without further purification.

Aufarbeitung

  1. additionThe mixture was poured on ice/sodium bicarbonate solution
  2. customthe organic phase separated
  3. extractionThe water phase is extracted with dichloromethane
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (sodium sulphate)
  6. customevaporated
  7. customthe obtained material (174 mg, 81%) used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-b04acf9a30034fa1a1080466a7e92ccd
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429605B2

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