Lithium bis((trifluoromethyl)sulfonyl)azanide → 3-Ethyl-2-methylbenzothiazolium bis(trifluoromethanesulfonyl)imide

HRID 547880Notes

Reaction equation

HRID 547880 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]([N+:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[S:22][C:21]=1[CH3:29])[CH3:19]>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].[CH2:18]([N+:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[S:22][C:21]=1[CH3:29])[CH3:19]

Participants

4

Reactant 2

HCID 3816071Lithium bis((trifluoromethyl)sulfonyl)azanideHCID 128599783-Ethyl-2-methyl-1,3-benzothiazol-3-ium bromide

Product 1

HCID 1317288313-Ethyl-2-methylbenzothiazolium bis(trifluoromethanesulfonyl)imideYield 88.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.22 g (7.73 mmol) of lithium bis(trifluoromethanesulfonyl)imide, Li[(CF3SO2)2N], in 5 ml of water are added dropwise with stirring to a solution of 2.00 g (7.75 mmol) of 3-ethyl-2-methylbenzothiazolium bromide in 50 ml of water. The lower liquid phase is extracted a number of times with 50 ml of dichloromethane, and the combined organic phases are dried using Mg2SO4. The solvent is subsequently removed by distillation, and the residue is dried under a reduced pressure of 1.3 Pa at 60° C., giving 3.14 g of 3-ethyl-2-methylbenzothiazolium bis(trifluoromethanesulfonyl)imide, corresponding to a yield of 88.7%.

Workup

  1. extractionThe lower liquid phase is extracted a number of times with 50 ml of dichloromethane
  2. customthe combined organic phases are dried
  3. customThe solvent is subsequently removed by distillation
  4. customthe residue is dried under a reduced pressure of 1.3 Pa at 60° C.

Sources & evidence

ORD record
ord-0574fb0a135e4658a9f6d5bd4eafa912
Source dataset
uspto-grants-2011_05
Patent number
US07939644B2

Reaction notes

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