Epichlorohydrin → n-Glycidyl-n-methylperfluorobutanesulfonamide

HRID 2099910

Reaktionsgleichung

Reaktionsgleichung von HRID 2099910
[C:1]([S:14]([NH:17][CH3:18])(=[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].[CH2:19]([CH:21]1[O:23][CH2:22]1)Cl>>[CH3:18][N:17]([CH2:19][CH:21]1[CH2:22][O:23]1)[S:14]([C:1]([F:3])([F:2])[C:4]([F:6])([F:5])[C:7]([F:9])([F:8])[C:10]([F:13])([F:11])[F:12])(=[O:15])=[O:16]

Komponenten

3

Edukt 2

HCID 7835EpichlorohydrinHCID 1099681,1,2,2,3,3,4,4,4-nonafluoro-N-methylbutane-1-sulfonamide

Produkt 1

HCID 86614459n-Glycidyl-n-methylperfluorobutanesulfonamideAusbeute 42 %

Reaktionsbedingungen

Temperatur
64 °C

Versuchsvorschrift

A mixture of C4F9SO2NHCH3 (313 g, 1.00 mol), generally made as described in U.S. Pat. No. 6,664,354, Example 1, Part A, and sodium methoxide (216 g of a 25% solution in methanol) was concentrated to a solid, which was dissolved in dry THF (500 mL). Epichlorohydrin (120.2 g, 1.3 mol) was rapidly added to the resulting solution, and the mixture was stirred at reflux (64° C.) for 20 hours. The cooled mixture was washed with about 1 L of water, and dichloromethane was used to help transfer the organic fraction. The organic fraction was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by one-plate distillation [bp 90° C./0.06 mmHg (8 Pa)] to provide 155.2 g of N-methyl-N-(oxiran-2-ylmethyl)perfluorobutane-1-sulfonamide, which was 98% pure by GLC.

Aufarbeitung

  1. concentration6,664,354, Example 1, Part A, and sodium methoxide (216 g of a 25% solution in methanol) was concentrated to a solid, which
  2. dissolutionwas dissolved in dry THF (500 mL)
  3. washThe cooled mixture was washed with about 1 L of water, and dichloromethane
  4. dry with materialThe organic fraction was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. distillationThe residue was purified by one-plate distillation [bp 90° C./0.06 mmHg (8 Pa)]

Quellen und Nachweise

ORD-Eintrag
ord-1c01f4c906414017b7333b2ad18be809
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569715B2

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