Dimethylformamide → 3-Benzyloxy-4-methoxy-4'-phenoxypicolinanilide

HRID 350639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350639
[CH2:1]([O:8][C:9]1[C:10]([C:17]([OH:19])=O)=[N:11][CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.CN(C=O)C.[O:37]([C:44]1[CH:50]=[CH:49][C:47]([NH2:48])=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>O>[CH2:1]([O:8][C:9]1[C:10]([C:17]([NH:48][C:47]2[CH:46]=[CH:45][C:44]([O:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[CH:50][CH:49]=2)=[O:19])=[N:11][CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6228Dimethylformamide2×HCID 8764(4-Aminophenoxy)benzeneHCID 682631,1'-CarbonyldiimidazoleHCID 199602893-Benzyloxy-4-methoxypicolinic acid

Produkt 1

HCID 178176673-Benzyloxy-4-methoxy-4'-phenoxypicolinanilideAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

3-Benzyloxy-4-methoxypicolinic acid (0.65 g, 2.5 mmol) and 0.50 g (3.0 mmol) of carbonyldiimidazole were mixed into anhydrous DMF to prepare a suspension (8 ml). An anhydrous DMF solution (2 ml) of 0.56 g (3.0 mmol) of 4-phenoxyaniline was added dropwise to this suspension, and a reaction was allowed to proceed at room temperature overnight. Water (10 ml) was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the dried organic layer was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane) to give 0.76 g (yield 71%) of the title compound.

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationthe dried organic layer was concentrated under the reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-43c855f6117246d292cd21e192fa324e
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183278B1

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