Triethylamine → N-(3-chloro-4-(3-chlorophenoxy)phenyl)picolinamide

HRID 38243

Reaktionsgleichung

Reaktionsgleichung von HRID 38243
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].CCN(CC)CC.[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1)[NH2:22]>C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[C:21]([NH:22][C:8](=[O:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH:23]=[CH:24][C:25]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 176055343-Chloro-4-(3-chlorophenoxy)aniline

Produkt 1

HCID 42645239N-(3-chloro-4-(3-chlorophenoxy)phenyl)picolinamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

According to Scheme 3 Step 3: Picolinoyl chloride hydrochloride (1.52 mmol, 271 mg) and Et3N (3.05 mmol, 0.42 mL) were added sequentially to a solution of 3-chloro-4-(3-chlorophenoxy)aniline (1.02 mmol, 258 mg) in DCM (6 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The organic phase was washed with a saturated solution of NaHCO3 and with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (90:10) as eluent to afford N-(3-chloro-4-(3-chlorophenoxy)phenyl)picolinamide (0.52 mmol, 187 mg, 51%) as a white solid.

Aufarbeitung

  1. washThe organic phase was washed with a saturated solution of NaHCO3 and with brine
  2. dry with materialwas dried over MgSO4
  3. filtrationwas filtered
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4dd49d5ee1784637a7cfe86cc55f2823
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524726B2

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