Sodium hydride → HCID 19082079, compound

HRID 963295Notes

Reaction equation

HRID 963295 reaction equation
[Cl:1][C:2]1[C:3]([CH2:29][CH3:30])=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:28])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=2)=[CH:13][CH:12]=1.[H-].[Na+].Cl[C:34]([O:36][CH2:37][CH:38]([CH3:40])[CH3:39])=[O:35]>C(COC)OC>[Cl:1][C:2]1[C:3]([CH2:29][CH3:30])=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([C:34]([O:36][CH2:37][CH:38]([CH3:40])[CH3:39])=[O:35])[C:9](=[O:28])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:20][N:19]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62365Isobutyl chloroformateHCID 19082084HCID 19082084, compound

Product 1

HCID 19082079HCID 19082079, compoundYield 32.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

1.0 g (2.3 mmol) of N-(3-chloro-2-ethylpyridin-4-yl)-4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetamide was dissolved in 5 ml of dimethoxy ethane, and the solution was stirred at room temperature. Then, 0.067 g (2.8 mmol) of sodium hydride was gradually added thereto, and the mixture was further stirred for one hour at room temperature. Then, 2 ml of a 1,2-dimethoxyethane solution containing 0.38 g (2.8 mmol) of isobutyl chloroformate was dropwise added thereto at a temperature of from -5° to 0° C., and the mixture was stirred for 30 minutes at a temperature of from -5° to 0° C. and for one hour at room temperature. Then, the reaction solution was poured into ice water and 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 0.4 g of the desired product as a yellow viscous substance (refractive index nD20 =1.3582).

Workup

  1. stirringthe mixture was further stirred for one hour at room temperature
  2. additionwas dropwise added
  3. stirringat a temperature of from -5° to 0° C., and the mixture was stirred for 30 minutes at a temperature of from -5° to 0° C. and for one hour at room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThen, ethyl acetate was distilled off under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-981900809a334d7c933eca38bed602b1
Source dataset
uspto-grants-1998_06
Patent number
US05763463

Reaction notes

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