Lithium bis((trifluoromethyl)sulfonyl)azanide → HCID 131730140, compound

HRID 1800866Notes

Reaction equation

HRID 1800866 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+].[I-].[CH2:18]([N+:22]1([CH3:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:19][CH2:20][CH3:21]>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+:22]1([CH3:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 3816071Lithium bis((trifluoromethyl)sulfonyl)azanideHCID 22406041HCID 22406041, compound

Product 1

HCID 131730140HCID 131730140, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Procedure 1c—A slight excess of lithium bis(trifluoromethylsulfonyl)imide dissolved in water was added to an aqueous solution of 1-butyl-1-methyl-azepanium iodide and stirred at room temperature for approximately 5 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 liquid, 1-butyl-1-methylazepanium bis(trifluoromethylsulfonyl)imide. δH (500.13 MHz, CDCl3) 3.42 (2H, m), 3.36 (2H, m), 3.22 (2H, m), 3.02 (3H, s), 1.88 (4H, m), 1.73 (6H, m), 1.40 (2H, sextet), 1.00 (3H, t). δC (125.76 MHz, CDCl3) 120 (q, CF3), 65.56, 64.84, 50.55, 27.46, 24.49, 21.80, 19.54, 13.37. ESI-MS: m/z=170 [M]+ (100). Calcd. for C11H24N: 170.1909; found: 170.1912, m/z=280 [M]− (100). Calcd. for C2F6NO4S2: 279.9173; found: 279.9163; Tg=−80° C.

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-072f78709118402e93d8576f9e2cd688
Source dataset
uspto-grants-2013_01
Patent number
US08345407B2

Reaction notes

Loading…