1,1'-Carbonyldiimidazole → HCID 19082084, compound

HRID 963299Notes

Reaction equation

HRID 963299 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=O)=[CH:12][CH:11]=2)=[N:7][CH:8]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:34][C:35]1[CH:40]=[CH:39][N:38]=[C:37]([CH2:41][CH3:42])[C:36]=1[Cl:43]>>[Cl:43][C:36]1[C:37]([CH2:41][CH3:42])=[N:38][CH:39]=[CH:40][C:35]=1[NH:34][C:17](=[O:19])[CH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:21])[F:20])=[CH:8][N:7]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 117894634-Pyridinamine, 3-chloro-2-ethyl-HCID 19082076HCID 19082076, compound

Product 1

HCID 19082084HCID 19082084, compoundYield 59.9%

Procedure

3.6 g (12.1 mmol) of 4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetic acid was dissolved in 20 ml of 4dioxane, and the solution was stirred at room temperature. Then, 2.4 g (14.8 mmol) of 1,1'-carbonyldiimidazole was gradually added thereto, and the mixture was stirred for one hour at room temperature. Then, 1.8 g (11.5 mmol) of 4-amino-3-chloro-2-ethylpyridine was added thereto, and the mixture was refluxed under heating for 30 minutes. The reaction solution was concentrated, and the residue was extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 3.0 g of the desired product as colorless cotton-like crystals (melting point: 124.5° to 125° C.).

Workup

  1. stirringthe mixture was stirred for one hour at room temperature
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 30 minutes
  4. concentrationThe reaction solution was concentrated
  5. extractionthe residue was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThen, ethyl acetate was distilled off under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e9bdc17b14ff4f2f9603f8b4c2a8a230
Source dataset
uspto-grants-1998_06
Patent number
US05763463

Reaction notes

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