Methyl iodide → HCID 86754840, compound

HRID 1603842Notes

Reaction equation

HRID 1603842 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[F:7][C:8]([F:39])([F:38])[C:9]([NH:11][C:12]1[C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=[CH:31][C:13]=1[O:14][CH2:15][CH2:16][N:17]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])=[O:10].CI>>[CH3:1][C:13]1([CH:31]=[CH:32][CH:33]=[C:34]([N+:35]([O-:37])=[O:36])[CH:12]1[NH:11][C:9](=[O:10])[C:8]([F:38])([F:39])[F:7])[O:14][CH2:15][CH2:16][N:17]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:18](=[O:23])[C:19]([F:21])([F:20])[F:22]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86754839HCID 86754839, compound

Product 1

HCID 86754840HCID 86754840, compoundYield 93.3%

Procedure

A suspension of potassium carbonate (1.44 g, 10.4 mmol), N-[2-(2-{2,2,2-trifluoroacetamidyl}-3-nitro-phenoxy)-ethyl]-N-benzyl-2,2,2-trifluoro-acetamide (1.0 g, 2.09 mmol) and methyl iodide (2.96 g, 20.9 mmol, previously filtered through basic alumina) in anhydrous dimethylsulfoxide (11 mL) was allowed to stir at room temperature for 24 h. The reaction mixture was poured into methylene chloride (200 mL) and extracted with water (2×80 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum to afford a yellow thick oil. Purification by chromatography (30% ethyl acetate-hexanes) afforded 960 mg (93.3%) of a light yellow solid, mp 90-92.5° C.; MS m/e EI 493 (M+).

Workup

  1. filtrationpreviously filtered through basic alumina) in anhydrous dimethylsulfoxide (11 mL)
  2. additionThe reaction mixture was poured into methylene chloride (200 mL)
  3. extractionextracted with water (2×80 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under vacuum
  7. customto afford a yellow thick oil
  8. customPurification by chromatography (30% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-17df2c1f5026427da97c542f41df9c5b
Source dataset
uspto-grants-1999_11
Patent number
US05990144

Reaction notes

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