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

HRID 350639Notes

Reaction equation

HRID 350639 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 178176673-Benzyloxy-4-methoxy-4'-phenoxypicolinanilideYield 71.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-43c855f6117246d292cd21e192fa324e
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Reaction notes

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