Lithium bis((trifluoromethyl)sulfonyl)azanide → 6-Azonia-spiro[5,6]dodecane bis[(trifluoromethyl)sulfonyl]imide

HRID 416461Notes

Reaction equation

HRID 416461 reaction equation
[N-:1]([S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])[S:2]([C:5]([F:8])([F:7])[F:6])(=[O:4])=[O:3].[Li+].[Br-].[CH2:18]1[N+:23]2([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:22][CH2:21][CH2:20][CH2:19]1>O>[N-:1]([S:2]([C:5]([F:8])([F:6])[F:7])(=[O:4])=[O:3])[S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10].[CH2:22]1[N+:23]2([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 3816071Lithium bis((trifluoromethyl)sulfonyl)azanideHCID 173656566-Azaspiro[5.6]dodecan-6-ium bromide

Product 1

HCID 601452806-Azonia-spiro[5,6]dodecane bis[(trifluoromethyl)sulfonyl]imide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A slight excess of lithium bis[(trifluoromethyl)sulfonyl]imide dissolved in water was added to an aqueous solution of 6-azonia-spiro[5,6]dodecane bromide and stirred at room temperature for several hours. The reaction mixture was transferred to a separating funnel and the heavy layer washed several times with water. The addition of a small amount of dichloromethane aided the separation of the aqueous and organic layer. The heavy organic layer was then evaporated to dryness leaving a pale yellow solid, 6-azonia-spiro[5,6]dodecane bis[(trifluoromethyl)sulfonyl]imide with a melting point of 96° C. ES/MS 168 (Cation C11H22N), −280 (Anion C2F6NS2O4).

Workup

  1. customThe reaction mixture was transferred to a separating funnel
  2. washthe heavy layer washed several times with water
  3. additionThe addition of a small amount of dichloromethane
  4. customthe separation of the aqueous and organic layer
  5. customThe heavy organic layer was then evaporated to dryness

Sources & evidence

ORD record
ord-b3ce2ab816f644c9bb7da91ace2f4949
Source dataset
uspto-grants-2012_01
Patent number
US08088917B2

Reaction notes

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