Ethanol → HCID 14076670, compound

HRID 4754Notes

Reaction equation

HRID 4754 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[C:10]([C:12]([OH:21])([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:8][C:7]=1[CH2:22][CH2:23][C:24]([N:26]([CH3:28])[CH3:27])=[O:25])([O-:5])=[O:4].CI.[CH2:31](O)C>CN(C)C=O.O>[N+:3]([C:6]1[CH:11]=[C:10]([C:12]([O:21][CH3:31])([C:13]([F:14])([F:15])[F:16])[C:17]([F:18])([F:19])[F:20])[CH:9]=[CH:8][C:7]=1[CH2:22][CH2:23][C:24]([N:26]([CH3:28])[CH3:27])=[O:25])([O-:5])=[O:4]

Participants

7

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14076664HCID 14076664, compound

Product 1

HCID 14076670HCID 14076670, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 2.15 (0.085 mole) of sodium hydride in 200 ml dimethylformamide is added 29.1 g (0.075 mole) of 3-{2-nitro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-N,N-dimethylpropanamide in in 50 ml dimethylformamide at such a rate that excessive foaming is avoided. To the resulting suspension, stirred in a nitrogen atmosphere, is added 14.2 g (0.10 mole) of methyl iodide to give a reaction mixture, which is stirred at room temperature overnight. The reaction mixture is then treated with 5 ml of ethanol, poured into 1-liter of water and extracted with ether. The resulting ether solution is washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated at reduced pressure to obtain a residual oil which is chromatographed on Silicar® CC-7. Elution with chloroform gives a major fraction consisting of 16 g which is recrystallized from hexane to give 3-{2-nitro-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl}-N,N-dimethylpropanamide having a melting point of 51° -54°.

Workup

  1. customto give a reaction mixture, which
  2. stirringis stirred at room temperature overnight
  3. extractionextracted with ether
  4. washThe resulting ether solution is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated at reduced pressure
  8. customto obtain a residual oil which
  9. customis chromatographed on Silicar® CC-7
  10. washElution with chloroform
  11. customgives a major fraction
  12. customis recrystallized from hexane

Sources & evidence

ORD record
ord-6f660a7817ea40438cb69e468c18825b
Source dataset
uspto-grants-1988_02
Patent number
US04727180

Reaction notes

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