Allyl bromide → N-Allyl-N-methylnonafluorobutanesulfonamide

HRID 1408499

Reaction equation

HRID 1408499 reaction equation
[CH3:1][NH:2][S:3]([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])(=[O:5])=[O:4].C[O-].[Na+].[CH2:22](Br)[CH:23]=[CH2:24]>CO.C1COCC1.O>[CH2:22]([N:2]([CH3:1])[S:3]([C:6]([F:17])([F:18])[C:7]([F:15])([F:16])[C:8]([F:13])([F:14])[C:9]([F:10])([F:12])[F:11])(=[O:5])=[O:4])[CH:23]=[CH2:24]

Participants

7

Reactant 3

HCID 7841Allyl bromideHCID 1099681,1,2,2,3,3,4,4,4-nonafluoro-N-methylbutane-1-sulfonamideHCID 10942334Sodium Methoxide

Product 1

HCID 86663271N-Allyl-N-methylnonafluorobutanesulfonamideYield 91.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of 313 g (1 mol) N-methylnonafluorobutanesulfonamide (3M Co., U.S. Pat. No. 6,664,354, Savu), 216 g (1 mol) 25% sodium methoxide in methanol (Aldrich), and 100 mL THF (EMD) was stirred at 50° C. for one hour and stripped. The residue was diluted with 600 mL THF and treated with 100 mL (1.15 mol) allyl bromide (Aldrich). The mixture was stirred at 40° C. for about 8 hr and then diluted with water. Extraction with methylene chloride and distillation yielded 321.7 g colorless liquid, by 75-80° C./1.1 mm Hg.

Workup

  1. extractionExtraction
  2. distillationwith methylene chloride and distillation

Sources & evidence

ORD record
ord-132f713265a1453197029d35e2841a90
Source dataset
uspto-grants-2014_12
Patent number
US08920679B2

Linked notes

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