Sodium hydride → HCID 22327360, compound

HRID 495650Notes

Reaction equation

HRID 495650 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:9]([F:12])([F:11])[F:10])[C:3]=1[N:13]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])[C:14](=[O:18])OCC.[H-].[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:8][C:6]1[CH:5]=[C:4]([C:9]([F:10])([F:11])[F:12])[C:3]2[N:13]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[C:14](=[O:18])[NH:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 22327372HCID 22327372, compound

Product 1

HCID 22327360HCID 22327360, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2,4-diamino-6-(trifluoromethyl)phenyl(2,4-dichlorophenyl)carbamate (1.1454 g) was dissolved in ethanol (20 ml), and to the solution was added sodium hydride (112.2 mg). The reaction mixture was heated at reflux for 6 hours. After allowing to cool, to the reaction mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (60 g, CHCl3:methanol=10:1→5:1) to give the title compound (0.8058 g, 79%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 6 hours
  3. temperatureto cool, to the reaction mixture
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was purified by silica gel column (60 g, CHCl3:methanol=10:1→5:1)

Sources & evidence

ORD record
ord-e1257daee7ab48e89a4ecf30d7e85b4c
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

Loading…