Hydrochloric Acid → N-(3-Acetyl-5-pentafluorosulfanylphenyl)-N-ethyl-2,2,2-trifluoroacetamide

HRID 1258505Notes

Reaction equation

HRID 1258505 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH:7]=[C:8]([S:10]([F:15])([F:14])([F:13])([F:12])[F:11])[CH:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:30][CH3:31].IC.Cl>C(COC)OC.C(OCC)(=O)C.O>[C:1]([C:4]1[CH:5]=[C:6]([N:16]([CH2:30][CH3:31])[C:17](=[O:22])[C:18]([F:21])([F:19])[F:20])[CH:7]=[C:8]([S:10]([F:14])([F:15])([F:13])([F:12])[F:11])[CH:9]=1)(=[O:3])[CH3:2]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 58085708HCID 58085708, compound

Product 1

HCID 58137469N-(3-Acetyl-5-pentafluorosulfanylphenyl)-N-ethyl-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

N-(3-Acetyl-5-pentafluorosulfanylphenyl)-2,2,2-trifluoroacetamide (100 mg, example 4d) was dissolved in absolute dimethoxyethane (5 ml) in a microwave insert and admixed with powdered potassium carbonate (40 mg). After adding iodoethane (60 μl), the mixture was heated to 100° C. in the microwave for 30 min. Subsequently, further iodomethane (60 μl) was added and the mixture was heated again to 100° C. for 30 min. This operation was repeated once more. Then the mixture was worked up by adding it to a mixture of water, ethyl acetate and 1 N HCl. Removal of the organic phase was followed by extraction three times more 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 three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 50 mg of the desired compound were obtained.

Workup

  1. temperaturethe mixture was heated again to 100° C. for 30 min
  2. additionby adding it
  3. customRemoval of the organic phase
  4. extractionwas followed by extraction three times more 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 three times with ethyl acetate
  10. dry with materialThe combined extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-7bec71f5bf274a7081dbb73ce36c7ede
Source dataset
uspto-grants-2013_06
Patent number
US08466169B2

Reaction notes

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