[C:1]([S:14]([NH2:17])(=[O:16])=[O:15])([C:4]([C:7]([C:10]([F:13])([F:12])[F:11])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2].[OH-].[Na+].Cl[CH2:21][C:22]([O:24][Na:25])=[O:23]>O>[C:1]([S:14]([NH:17][CH2:21][C:22]([O:24][Na:25])=[O:23])(=[O:16])=[O:15])([C:4]([C:7]([C:10]([F:13])([F:11])[F:12])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2]A 1 L 3-necked round bottom flask equipped with a mechanical stirrer, thermocouple, reflux condenser and heating mantle was charged with C4F9SO2NH2 (58 g; 0.20 moles; as prepared above), NaOH (8.7 g; 0.22 moles; pellets) and water (60 mL) and heated at 98° C. for 45 minutes. Upon cooling to 76° C., ClCH2CO2Na (25 g; 0.22 moles, Sigma-Aldrich) was added and the temperature was then increased to 100° C. and maintained for 18 hours. Water was then added (200 mL) and a white solid appeared. The upper liquid phase was decanted off and discarded leaving the white solid, to which water (250 mL) was added. Water was removed to yield C4F9SO2N(H)CH2CO2Na (53.1 g ; 74% yield).
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