Triethylamine → N-Decylperfluorooctanesulfonamide

HRID 567641

Reaction equation

HRID 567641 reaction equation
[F:1][C:2]([F:29])([S:25](F)(=[O:27])=[O:26])[C:3]([F:24])([F:23])[C:4]([F:22])([F:21])[C:5]([F:20])([F:19])[C:6]([F:18])([F:17])[C:7]([F:16])([F:15])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10].C(N(CC)CC)C.[CH2:37]([NH2:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>O>[CH2:37]([NH:47][S:25]([C:2]([F:29])([F:1])[C:3]([F:23])([F:24])[C:4]([F:22])([F:21])[C:5]([F:20])([F:19])[C:6]([F:17])([F:18])[C:7]([F:15])([F:16])[C:8]([F:13])([F:14])[C:9]([F:11])([F:12])[F:10])(=[O:27])=[O:26])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8916DecylamineHCID 9388Perfluorooctanesulfonyl fluoride

Product 1

HCID 22352717N-Decylperfluorooctanesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50.21 g (100.0 mmol) of perfluorooctanesulfonyl fluoride is added in drops to a mixture of 10.62 g (105.0 mmol) of triethylamine and 15.73 g (100.0 mmol) of decylamine at 80° C. while being stirred vigorously. It is stirred for 2 days at 80° C., the reaction mixture is mixed with 300 ml of water and extracted three times with ethyl acetate. The combined organic extracts are dried on sodium sulfate, filtered and concentrated by evaporation. The residue is chromatographed on silica gel (mobile solvent: dichloromethane/methanol=4/1).

Workup

  1. stirringIt is stirred for 2 days at 80° C.
  2. extractionextracted three times with ethyl acetate
  3. customThe combined organic extracts are dried on sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. customThe residue is chromatographed on silica gel (mobile solvent: dichloromethane/methanol=4/1)

Sources & evidence

ORD record
ord-7fcaca3ced1f477e9b6b32890d45deff
Source dataset
uspto-grants-2001_01
Patent number
US06180113B2

Linked notes

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