Sulfuric Acid → N-Methyl perfluoro-1-ethane sulfonamide

HRID 901316Notes

Reaction equation

HRID 901316 reaction equation
[C:1]([S:8](F)(=[O:10])=[O:9])([C:4]([F:7])([F:6])[F:5])([F:3])[F:2].[CH3:12][NH2:13].S(=O)(=O)(O)O.[CH3:19][C:20]([O:23]C)(C)C>>[C:1]([S:8]([N:13]([CH2:19][CH2:20][OH:23])[CH3:12])(=[O:10])=[O:9])([C:4]([F:7])([F:6])[F:5])([F:3])[F:2].[C:1]([S:8]([NH:13][CH3:12])(=[O:10])=[O:9])([C:4]([F:7])([F:6])[F:5])([F:3])[F:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6329MethylamineHCID 15413tert-Butyl methyl etherHCID 6451567Ethanesulfonyl fluoride, 1,1,2,2,2-pentafluoro-

Product 2

HCID 59030189N-Methyl perfluoro-1-ethane sulfonamideHCID 86057590C2F5SO2N(CH3)CH2CH2OH

Procedure

C2F5SO2N(CH3)CH2CH2OH was prepared from C2F5SO2F by reaction with monomethylamine in MTBE, followed by stripping of the solvent, acidification with 19% sulfuric acid, then water washing and distillation at 5.5 mm at a head temperature of 69° C. to give C2F5SO2N(CH3)H. The C2F5SO2N(CH3)H was then reacted with 3 equivalents of ethylene carbonate and 0.08 equivalents K2CO3 neat at 110° C. overnight. The product was isolated by successive washes with water, 3% sulfuric acid and water, followed by distillation at 0.5 mm at a head temperature of 98° C.

Workup

  1. distillationwater washing and distillation at 5.5 mm at a head temperature of 69° C.

Sources & evidence

ORD record
ord-f598fb5eec98446bbaaf5a54ee7ce9b8
Source dataset
uspto-grants-2008_04
Patent number
US07361782B2

Reaction notes

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