Sodium Hydroxide → HCID 178521362, compound

HRID 1375299Notes

Reaction equation

HRID 1375299 reaction equation
[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]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10958205PerfluorobutanesulfonamideHCID 178520815HCID 178520815, compound

Product 1

HCID 178521362HCID 178521362, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
98 °C

Procedure

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).

Workup

  1. customA 1 L 3-necked round bottom flask equipped with a mechanical stirrer
  2. temperaturethermocouple, reflux condenser
  3. temperatureheating mantle
  4. temperatureUpon cooling to 76° C.
  5. temperaturethe temperature was then increased to 100° C.
  6. temperaturemaintained for 18 hours
  7. customThe upper liquid phase was decanted off
  8. customdiscarded leaving the white solid
  9. customWater was removed

Sources & evidence

ORD record
ord-3d30991f84fe45bfb63a78adae7c035f
Source dataset
uspto-grants-2007_01
Patent number
US07169323B2

Reaction notes

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