Methyl iodide → HCID 14564861, compound

HRID 1164968Notes

Reaction equation

HRID 1164968 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[CH3:22]I.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:22])[C:14](=[O:19])[C:15]([F:17])([F:18])[F:16])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 592128Acetamide, N-(2-(3,4-dimethoxyphenyl)ethyl)-2,2,2-trifluoro-

Product 1

HCID 14564861HCID 14564861, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 20.0 9 (0.07 mol) of N-[2-(3,4-dimethoxyphenyl)ethyl]trifluoroacetamide to a suspension of 3.17 g (0.08 mol) of 60% sodium hydride in 50 mL of dry tetrahydrofuran. Stir this suspension for 30 minutes at room temperature. After 30 minutes, add 6.72 mL (0.11 mol) of methyl iodide and stir at room temperature for one h. After one h, filter reaction mixture and make basic (pH=14) with 4N sodium hydroxide. Wash this mixture with 2×100 mL of water. Extract the combined aqueous washes with 2×100 mL of methylene chloride. Wash the combined organic extracts with 6N hydrochloric acid, then with 100 mL of water. Dry the organic layer over anhydrous sodium sulfate. Filter the drying agent and remove the solvent in vacuo to provide the title compound.

Workup

  1. waitAfter 30 minutes
  2. stirringstir at room temperature for one h
  3. filtrationAfter one h, filter
  4. customreaction mixture
  5. washWash this mixture with 2×100 mL of water
  6. extractionExtract the combined aqueous washes with 2×100 mL of methylene chloride
  7. washWash the combined organic extracts with 6N hydrochloric acid
  8. dry with materialDry the organic layer over anhydrous sodium sulfate
  9. filtrationFilter the drying agent
  10. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-ba14d57f9aaf4509b9e70a5ca0c2994f
Source dataset
uspto-grants-1990_03
Patent number
US04906634

Reaction notes

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