Water → HCID 178457459, compound

HRID 2211563Notes

Reaction equation

HRID 2211563 reaction equation
[C:1]([S:14]([NH:17][CH2:18][CH2:19][CH3:20])(=[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-:21].[Na+:22].[OH2:23]>>[C:1]([S:14]([N:17]([CH2:7][CH:4]([CH2:1][S:14]([O:16][Na:22])(=[O:15])=[O:23])[OH:21])[CH2:18][CH2:19][CH3:20])(=[O:15])=[O:16])([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

4

Reactant 3

HCID 962Water3×HCID 14798Sodium HydroxideHCID 22169334HCID 22169334, compound

Product 1

HCID 178457459HCID 178457459, compoundYield 81%

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 C4F9SO2NHC3H7 (93.6 g; 0.27 moles; as prepared above), NaOH (13.6 g; 0.35 moles; pellets) and water (90 mL) and heated at 98° C. for 45 minutes. Upon cooling to 76° C., CHPS (67.5 g; 0.34 moles) was added and the temperature was then increased to 100° C. and maintained for 18 hours. Water was then added (250 mL) and a viscous yellow liquid formed in the bottom of the flask. The upper liquid phase was decanted off and discarded leaving a thick yellow liquid, to which water (250 mL) was added. The temperature of the mixture was increased to 50° C., then cooled to 19° C. Upon removal of water a creme colored solid remained, C4F9SO2N(C3H7)CH2CH(OH)CH2SO3Na (111.4 g; 81% 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. additionCHPS (67.5 g; 0.34 moles) was added
  6. temperaturethe temperature was then increased to 100° C.
  7. temperaturemaintained for 18 hours
  8. customa viscous yellow liquid formed in the bottom of the flask
  9. customThe upper liquid phase was decanted off
  10. customdiscarded leaving a thick yellow liquid
  11. temperatureThe temperature of the mixture was increased to 50° C.
  12. temperaturecooled to 19° C
  13. customUpon removal of water a creme colored solid

Sources & evidence

ORD record
ord-516355133540418a8c75c072b8c097b6
Source dataset
uspto-grants-2006_09
Patent number
US07101492B2

Reaction notes

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