Sodium hydride → HCID 19082086, compound

HRID 963297Notes

Reaction equation

HRID 963297 reaction equation
[Cl:1][C:2]1[C:3]([CH2:13][CH3:14])=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:12])[O:10][CH3:11].[H-].[Na+].[F:17][C:18]([F:37])([F:36])[C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]2[CH:31]=[CH:30][C:29]([CH2:32][C:33](Cl)=[O:34])=[CH:28][CH:27]=2)=[N:23][CH:24]=1.C(=O)([O-])O.[Na+]>CN(C)C(=O)C>[Cl:1][C:2]1[C:3]([CH2:13][CH3:14])=[N:4][CH:5]=[CH:6][C:7]=1[N:8]([C:9]([O:10][CH3:11])=[O:12])[C:33](=[O:34])[CH2:32][C:29]1[CH:28]=[CH:27][C:26]([O:25][C:22]2[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:37])[F:36])=[CH:24][N:23]=2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 19082070HCID 19082070, compoundHCID 19082082HCID 19082082, compound

Product 1

HCID 19082086HCID 19082086, compoundYield 26.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2.0 g (9.3 mmol) of methyl N-(3-chloro-2-ethylpyridin-4-yl)-carbamate was dissolved in 10 ml of N,N-dimethylacetamide, and the solution was stirred at room temperature. Then, 0.27 g (11.2 mmol) of sodium hydride was gradually added thereto, and the mixture was stirred for one hour at room temperature. Then, 5.5 g (17.4 mmol) of 4-[(5-trifluoromethylpyridin-2-yl)oxy]phenylacetyl chloride was dropwise added thereto at -15° C., and the mixture was stirred for 3 hours at a temperature of from -15° to -10° C. Then, the reaction solution was poured into a sodium hydrogen carbonate solution cooled with ice 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) and further purified by a thin layer chromatography to obtain 1.2 g of the desired product as a white powder (melting point: 62° to 64° C.).

Workup

  1. stirringthe mixture was stirred for one hour at room temperature
  2. stirringat -15° C., and the mixture was stirred for 3 hours at a temperature of from -15° to -10° C
  3. temperaturecooled with ice
  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)
  9. customfurther purified by a thin layer chromatography

Sources & evidence

ORD record
ord-17132567e45a434aba9350adcb39dc9f
Source dataset
uspto-grants-1998_06
Patent number
US05763463

Reaction notes

Loading…