Trifluoroacetic acid → HCID 23150795, compound
Reaction equation
C([NH:5][S:6]([C:9]1[C:14]([I:15])=[CH:13][CH:12]=[CH:11][C:10]=1[F:16])(=[O:8])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>>[F:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([I:15])[C:9]=1[S:6]([NH2:5])(=[O:7])=[O:8]Participants
Procedure
30.00 g (99.64 mmol) of 2-fluoro-6-iodobenzenesulfonamide, obtained from the reaction of N-(tert-butyl)-2-fluoro-6-iodobenzenesulfonamide with trifluoroacetic acid in analogy to example A3, are introduced together with 15.15 g (109.61 mmol) of potassium carbonate in 250 ml of dimethylformamide. At room temperature 7.68 g (109.61 mmol) of sodium thiomethoxide are added in portions, after which the mixture is stirred at room temperature for 12 h. It is poured into 150 ml of ice-water, adjusted to a pH of 4-5 using 2 N hydrochloric acid, and extracted with ethyl acetate. The organic phase is dried and evaporated. Preparative HPLC (reversed phase, 0.05% trifluoroacetic acid in water/acetonitrile, gradient: in 30 min, 25% to 100% acetonitrile) gives 7.40 g (23% of theory) of 2-iodo-6-(methylthio)benzenesulfonamide.
Sources & evidence
- ORD record
- ord-0af6513f258543fc87ca2c857e5427b6
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855166B2
Reaction notes
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