HCID 178506935, compound → Bis(trifluoromethane)sulfonimide

HRID 1603251Notes

Reaction equation

HRID 1603251 reaction equation
[Li][N:2]([S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11])[S:3]([C:6]([F:9])([F:8])[F:7])(=[O:5])=[O:4]>S(=O)(=O)(O)O>[NH:2]([S:3]([C:6]([F:9])([F:7])[F:8])(=[O:5])=[O:4])[S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11]

Participants

3

Reactant 1

HCID 178506935HCID 178506935, compound

Product 1

HCID 157857Bis(trifluoromethane)sulfonimideYield 75.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The imide HN(SO2CF3), was obtained from the lithium salt. LiN(SO2CF3)2 (10 g, 35 mmole) was added to 50 mL concentrated sulfuric acid. The free imide was distilled at about 90° C., 10 mm Hg and purified by sublimation at about 70° C., 1-2 mm Hg giving 7.4 g (74%) HN(SO2CF3)2. The silver salt was then obtained from the imide. Ag2CO3 (2.0 g, 0.2 mmol) was added slowly to a stirring, solution of HN(SO2CF3)2 (3.5 g, 12.0 mmole) in 25 mL water. The mixture was then digested, wrapped in foil, at 60° C. for 1 h and the excess Ag2CO3 filtered off. The water was removed under vacuum giving white powder of AgNTf2. Dissolution of the powder in diethyl ether (25 mL) followed by filtration and removal of all volatiles under vacuum gave 4.6 g (95%) of white AgNTf2.

Workup

  1. distillationThe free imide was distilled at about 90° C.
  2. custom10 mm Hg and purified by sublimation at about 70° C.

Sources & evidence

ORD record
ord-2145ca0998694a1b9556477febad4fa7
Source dataset
uspto-grants-1999_11
Patent number
US05986120

Reaction notes

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