Pyridine → N-(1-chloro-2,2,2-trifluoroethyl)-4-methylbenzamide

HRID 479471

Reaktionsgleichung

Reaktionsgleichung von HRID 479471
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9](O)[C:10]([F:13])([F:12])[F:11])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:25])=O>C(Cl)Cl>[Cl:25][CH:9]([NH:8][C:6](=[O:7])[C:5]1[CH:15]=[CH:16][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:10]([F:13])([F:12])[F:11]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 121503224-methyl-N-(2,2,2-trifluoro-1-hydroxyethyl)benzamide

Produkt 1

HCID 12150323N-(1-chloro-2,2,2-trifluoroethyl)-4-methylbenzamideAusbeute 63,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A stirred solution of Example 1A (3.48 g, 15.0 mmol) in CH2Cl2 (60 mL) at 0° C. was treated with pyridine (1.20 mL). The reaction mixture was treated dropwise with thionyl chloride (1.10 mL, 15.0 mmol), and the reaction flask was equipped with a calcium chloride drying tube. The reaction mixture was stirred at 0° C. for 4 hours, the cooling bath was removed, and the solution was stirred at ambient temperature for an additional 12 hours. Concentration of the reaction mixture provided a white solid which was triturated with diethyl ether (2×200 mL) to provide 2.40 g of the desired product as a white solid.

Aufarbeitung

  1. customthe reaction flask was equipped with a calcium chloride drying tube
  2. customthe cooling bath was removed
  3. stirringthe solution was stirred at ambient temperature for an additional 12 hours
  4. customConcentration of the reaction mixture provided a white solid which
  5. customwas triturated with diethyl ether (2×200 mL)

Quellen und Nachweise

ORD-Eintrag
ord-d28284691f8040318f5a67ad89dcfc2e
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645968B2

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