Dimethylformamide → HCID 86709875, Verbindung

HRID 2167213Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2167213
[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 treated with methanol and dimethylaminopyridine indicated complete conversion of the starting material. Reaction was allowed to cool to room temperature and then 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, LRMS Calcd. C12H6Cl3NO: 284.95. Found: m/z=285 (M+), 250 (M+-Cl), 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-4d6800169f1849d3b4ea202a71fe2e1b
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045427B2

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