Methyl iodide → N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]-2,2,2-trifluoro-N-methylacetamide

HRID 1907826Notes

Reaction equation

HRID 1907826 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[C:9]([C:12]1[CH:13]=[C:14]([NH:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH:15]=[C:16]([S:18]([F:23])([F:22])([F:21])([F:20])[F:19])[CH:17]=1)(=[O:11])[CH3:10]>C(COC)OC>[C:9]([C:12]1[CH:13]=[C:14]([N:24]([CH3:1])[C:25](=[O:30])[C:26]([F:29])([F:27])[F:28])[CH:15]=[C:16]([S:18]([F:22])([F:23])([F:21])([F:20])[F:19])[CH:17]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58085708HCID 58085708, compound2×

Product 1

HCID 58136869N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]-2,2,2-trifluoro-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

In a microwave insert, N-(3-acetyl-5-pentafluorosulfanylphenyl)-2,2,2-trifluoroacetamide (0.25 g) was dissolved in absolute dimethoxyethane (7.5 ml), powdered potassium carbonate was added and the mixture was admixed with iodomethane (80 μl). Subsequently, the mixture was heated to 100° C. in the microwave for 40 min. Once further N-(3-acetyl-5-pentafluorosulfanylphenyl)-2,2,2-trifluoroacetamide (4×250 mg) had been converted in the manner described, the five batches were worked up together, having been decanted from the potassium carbonate into 1N hydrochloric acid while cooling with ice. After repeatedly washing the potassium carbonate residue with dimethoxyethane, the aqueous phase was extracted five times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed of the acetonitrile and extracted five times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 1.03 g of the desired compound were obtained.

Workup

  1. customhaving been decanted from the potassium carbonate into 1N hydrochloric acid
  2. temperaturewhile cooling with ice
  3. washAfter repeatedly washing the potassium carbonate residue with dimethoxyethane
  4. extractionthe aqueous phase was extracted five times with ethyl acetate
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by means of preparative HPLC
  9. extractionextracted five times with ethyl acetate
  10. dry with materialThe combined extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-8c2c4175d6044768bbe855c64d432e4f
Source dataset
uspto-grants-2013_12
Patent number
US08598177B2

Reaction notes

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