Dimethylformamide → HCID 86709875, Verbindung

HRID 541051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541051
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:15]([OH:17])=O)[CH:3]=1.S(Cl)([Cl:20])=O.CN(C)C=O.CN(C1C=CC=CN=1)C>C1(C)C=CC=CC=1.CO>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:15]([Cl:20])=[O:17])[CH:3]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 218852-DimethylaminopyridineHCID 24386Thionyl ChlorideHCID 86709876HCID 86709876, Verbindung

Produkt 1

HCID 86709875HCID 86709875, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 4,5-dichloro-6-phenylpicolinic acid (3.00 g, 11.2 mmol) in toluene (40 mL) was added thionyl chloride (1.22 mL, 16.8 mmol) and dimethylformamide (0.04 mL, 0.6 mmol). Reaction mixture was heated at 80° C. for 3 h. HPLC analysis of an aliquot of the reaction mixture treated with methanol and dimethylaminopyridine indicated complete conversion of the starting material. Reaction was allowed to cool to room temperature and concentrated under reduced pressure to provide a white solid. Toluene (40 mL) was added to dissolve the solid and concentrated under reduced pressure and then this process was performed a second time. 4,5-Dichloro-6-phenylpicolinoyl chloride was isolated as a white solid (2.84 g, 89% yield). 1H NMR (400 MHz, CDCl3) δ 8.14 (s, 1H), 7.83-7.75 (m, 2H), 7.55-7.47 (m, 3H); 13C NMR (101 MHz, CDCl3) δ 168.80, 158.88, 146.42, 145.21, 136.79, 134.40, 129.98, 129.61, 128.31, 124.74; MS: Calcd. for C12H6Cl3NO: 284.95. Found: 285 (M+), 250, 222, 187, 152; mp=106-111° C.

Aufarbeitung

  1. customReaction mixture
  2. customReaction
  3. temperatureto cool to room temperature
  4. concentrationconcentrated under reduced pressure
  5. customto provide a white solid
  6. dissolutionto dissolve the solid
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-da3b9de786144261a9b1c9cb7ca9006a
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871943B2

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