Methyl iodide → N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]-2,2,2-trifluoro-N-methylacetamide
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
Conditions
- Temperature
- 100 °C
Procedure
In a microwave insert, N-(3-acetyl-5-pentafluorosulfanylphenyl)-2,2,2-trifluoroacetamide (O3.075; 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 in the microwave to 100° C. 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, by decanting from potassium carbonate into 1 N hydrochloric acid with ice cooling. 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.
Workup
- customby decanting from potassium carbonate into 1 N hydrochloric acid with ice cooling
- washAfter repeatedly washing the potassium carbonate residue with dimethoxyethane
- extractionthe aqueous phase was extracted five times with ethyl acetate
- dry with materialThe combined extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8504d3eb01734f0394325d1dae8f36e4
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853206B2
Reaction notes
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