Water → N-Butyl-N-[(nonafluorobutyl)sulfonyl]glycine

HRID 1158606Notes

Reaction equation

HRID 1158606 reaction equation
[C:1]([S:14]([N:17]([CH2:22][C:23]([O:25]CC)=[O:24])[CH2:18][CH2:19][CH2:20][CH3:21])(=[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-].[K+].O>C(O)(C)C>[C:1]([S:14]([N:17]([CH2:22][C:23]([OH:25])=[O:24])[CH2:18][CH2:19][CH2:20][CH3:21])(=[O:15])=[O:16])([C:4]([C:7]([C:10]([F:11])([F:13])[F:12])([F:9])[F:8])([F:6])[F:5])([F:3])[F:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 131726677HCID 131726677, compound

Product 1

HCID 86068659N-Butyl-N-[(nonafluorobutyl)sulfonyl]glycine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
56 °C

Procedure

A one-liter flask fitted with a thermocouple, addition funnel, heating mantle, reflux condenser and overhead stirrer was charged with C4F9SO2NH(C4H9) (133.0 g; 0.375 mole), and sodium carbonate (33.0 g). The mixture was heated to 93° C. and ethyl bromoacetate (69.0 g; 0.411 mole) was slowly added over a period of 8 hours, and then the ensuing mixture was allowed to stir overnight at 93° C. To this mixture was added water (120.0 mL) and the temperature was 56° C., at which point sulfuric acid (39.0 g; concentrated) at a rate to keep the temperature below 100° C. Two phases formed and the bottom layer was recovered and washed with water (150 mL). This crude material was distilled (110-125° C.; 3.3 mm Hg) to yield C4F9SO2N(C4H9)CH2CO2C2H5 (107.0 g). A one-liter flask fitted with a thermocouple, addition funnel, heating mantle, reflux condenser and overhead stirrer was charged with C4F9SO2N(C4H9)CH2CO2C2H5 (103.0 g; 0.241 mole) KOH (18.0 g; 0.273 mole) water (50 mL) and isopropanol (50.0 g). The mixture was heated at reflux for 2 hours, and a Dean-Stark trap was added. As isopropanol was removed from the trap, an equivalent amount of water was added to the reaction mixture. When the reaction mixture reached 101° C. water (25 mL) was added and the mixture was cooled to 56° C.; upon addition of sulfuric acid (26.7 g; concentrated) the temperature rose to 78° C. and two phases appeared. The bottom phase was distilled (139-147° C.; 3.6 mm Hg) to yield a crème colored solid, C4F9SO2N(C4H9)CH2CO2H.

Workup

  1. customA one-liter flask fitted with a thermocouple, addition funnel
  2. temperatureheating mantle
  3. temperaturereflux condenser and overhead stirrer
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 2 hours
  6. additiona Dean-Stark trap was added
  7. customAs isopropanol was removed from the trap
  8. additionan equivalent amount of water was added to the reaction mixture
  9. customreached 101° C.
  10. additionwas added
  11. additionupon addition of sulfuric acid (26.7 g; concentrated) the temperature
  12. customrose to 78° C.
  13. distillationThe bottom phase was distilled (139-147° C.; 3.6 mm Hg)

Sources & evidence

ORD record
ord-ca0d455a087a44b388b665739406a8be
Source dataset
uspto-grants-2010_10
Patent number
US07811978B2

Reaction notes

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