Epichlorohydrin → HCID 14495223, compound

HRID 1602044Notes

Reaction equation

HRID 1602044 reaction equation
[CH3:1][NH:2][S:3]([C:6]([F:30])([F:29])[C:7]([F:28])([F:27])[C:8]([F:26])([F:25])[C:9]([F:24])([F:23])[C:10]([F:22])([F:21])[C:11]([F:20])([F:19])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])(=[O:5])=[O:4].[CH2:31]([CH:33]1[O:35][CH2:34]1)Cl.C[O-].[Na+].[OH-].[Na+]>CO.O>[CH3:1][N:2]([CH2:31][CH:33]1[O:35][CH2:34]1)[S:3]([C:6]([F:30])([F:29])[C:7]([F:27])([F:28])[C:8]([F:25])([F:26])[C:9]([F:23])([F:24])[C:10]([F:21])([F:22])[C:11]([F:19])([F:20])[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])(=[O:5])=[O:4]

Participants

7

Reactant 4

HCID 7835Epichlorohydrin2×HCID 14798Sodium HydroxideHCID 3034468N-MethylperfluorooctanesulfonamideHCID 10942334Sodium Methoxide

Product 1

HCID 14495223HCID 14495223, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

N-methyl-N-glycidyl-perfluorooctanesulfonamide ("epoxide A") was prepared by placing 450 grams N-methyl-perfluorooctanesulfonamide ("amide A") in a two-liter three-necked round-bottom flask and heating to 80° C., 101 grams epichlorohydrin was then added followed by 91 grams methanol. The temperature was reduced to 65° C. before 30 grams 25 wt % sodium methoxide in methanol solution was slowly added keeping the temperature below 70° C. 60 grams 50 wt % aqueous sodium hydroxide solution was slowly added keeping the temperature below 70° C. After addition the reaction was stirred at 65° C. overnight. Water-aspirator vacuum was applied to the flask and excess methanol and epichlorohydrin were removed. 450 grams water was then added to the flask with stirring at 65° to wash the product. The water was decanted after allowing the product to settle. This washing step was repeated a second time. Vacuum was applied to 20 mm Hg and the temperature of the flask was raised to 90° C. to remove volatile materials.

Workup

  1. additionwas slowly added
  2. customthe temperature below 70° C
  3. customthe temperature below 70° C
  4. additionAfter addition the reaction
  5. customwere removed
  6. addition450 grams water was then added to the flask
  7. stirringwith stirring at 65°
  8. washto wash the product
  9. customThe water was decanted
  10. temperaturethe temperature of the flask was raised to 90° C.
  11. customto remove volatile materials

Sources & evidence

ORD record
ord-194609f06e5b48c49d02c13ec156e6ae
Source dataset
uspto-grants-1999_11
Patent number
US05981038

Reaction notes

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