Ethylamine → N-Ethyl-perfluorobutane-1-sulfonamide

HRID 1769173Notes

Reaction equation

HRID 1769173 reaction equation
[F:1][C:2]([F:17])([S:13](F)(=[O:15])=[O:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].C(OC(C)C)(C)C.[CH2:25]([NH2:27])[CH3:26]>S(=O)(=O)(O)O>[CH2:25]([NH:27][S:13]([C:2]([F:17])([F:1])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6])(=[O:15])=[O:14])[CH3:26]

Participants

5

Reactant 3

HCID 6341EthylamineHCID 7914Diisopropyl EtherHCID 67814Perfluoro-1-butanesulfonyl fluoride

Product 1

HCID 14661392N-Ethyl-perfluorobutane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

N-ethyl-perfluorbutanesulfonamide (C4F9SO2N(H)CH2CH3) was prepared by placing 302 grams perfluorobutanesulfonyl fluoride and 500 mL diisopropyl ether in a two liter three-necked round bottom flask under nitrogen. Next 139.5 grams ethylamine (3.1 equivalents) was slowly added while keeping the temperature below 60° C. After addition was complete the reaction mixture was stirred at 60° C. overnight. Next, 500 milliliters of 6 M sulfuric acid was added. The organic layer was isolated and washed two times with equal volumes of water. The solvent was removed under reduced pressure the give the sulfonamide. The sulfonamides with varying Rf were prepared using this procedure but with the appropriate perfluoroalkanesulfonyl fluoride. The corresponding epoxides were prepared from these sulfonamides in the same manner as described in example 1.

Workup

  1. customthe temperature below 60° C
  2. additionAfter addition
  3. customThe organic layer was isolated
  4. washwashed two times with equal volumes of water
  5. customThe solvent was removed under reduced pressure the

Sources & evidence

ORD record
ord-2cc3cb603fba4afe8ae37f5d05a41314
Source dataset
uspto-grants-1995_01
Patent number
US05380778

Reaction notes

Loading…