Benzylamine → N-Hexyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide

HRID 567642

Reaction equation

HRID 567642 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]([NH2:44])[C:38]1C=[CH:42][CH:41]=[CH:40][CH:39]=1>O>[CH2:37]([NH:44][S:25]([C:2]([F:1])([F:29])[C:3]([F:23])([F:24])[C:4]([F:21])([F:22])[C:5]([F:20])([F:19])[C:6]([F:17])([F:18])[C:7]([F:15])([F:16])[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])(=[O:26])=[O:27])[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 9388Perfluorooctanesulfonyl fluoride

Product 1

HCID 22352711N-Hexyl-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50.21 g (100.0 mmol) of perfluoroctanesulfonyl fluoride is added in drops to a mixture of 10.62 g (105.0 mmol) of triethylamine and 10.12 g (100.0 mmol) of benzylamine 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-ea57f21b182844c78479c74f53aa608c
Source dataset
uspto-grants-2001_01
Patent number
US06180113B2

Linked notes

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