Pyridine → 4-Methyl-N-(1,2,2,2-tetrachloroethyl)benzamide

HRID 479490

Reaktionsgleichung

Reaktionsgleichung von HRID 479490
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9](O)[C:10]([Cl:13])([Cl:12])[Cl:11])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.S(Cl)([Cl:25])=O.C(OCC)C>C(Cl)Cl>[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]([Cl:25])[C:10]([Cl:13])([Cl:12])[Cl:11])=[O:7])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 33926644-methyl-N-(2,2,2-trichloro-1-hydroxyethyl)benzamide

Produkt 1

HCID 123415764-Methyl-N-(1,2,2,2-tetrachloroethyl)benzamideAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred solution of Example 37C (20.0 g, 70.8 mmol) in CH2Cl2(300 mL) at 0° C. was treated with pyridine (10 mL). The reaction mixture was treated dropwise with thionyl chloride (10.4 mL, 141 mmol), and the reaction flask was equipped with a calcium chloride drying tube. The reaction mixture was warmed to ambient temperature and stirred for 4 hours. Concentration of the reaction mixture to a reduced volume and addition of diethyl ether (100 mL) resulted in a precipitate which was filtered off, and the filtrate was concentrated and dried under reduced pressure to provide 19.0 g of the desired product as a white solid.

Aufarbeitung

  1. customthe reaction flask was equipped with a calcium chloride drying tube
  2. customresulted in a precipitate which
  3. filtrationwas filtered off
  4. concentrationthe filtrate was concentrated
  5. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3714a12322254811b07426d335532996
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645968B2

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