Acetonitrile → 2-[2-(Dimethylamino)ethylamino]succinic acid bis(3,3,4,4,5,5,6,6,6-nonafluorohexyl) ester

HRID 985370Notes

Reaction equation

HRID 985370 reaction equation
[C:1]([O:23][CH2:24][CH2:25][C:26]([F:38])([F:37])[C:27]([F:36])([F:35])[C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])(=[O:22])[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH2:8][C:9]([F:21])([F:20])[C:10]([F:19])([F:18])[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[O:5].CN[N:41]([CH2:44][CH3:45])NC.C(=O)([O-])[O-].[K+].[K+].[C:52](OCC)(=O)C.[C:58](#[N:60])C>>[CH3:52][N:60]([CH2:45][CH2:44][NH:41][CH:2]([CH2:3][C:4]([O:6][CH2:7][CH2:8][C:9]([F:21])([F:20])[C:10]([F:18])([F:19])[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])=[O:5])[C:1]([O:23][CH2:24][CH2:25][C:26]([F:37])([F:38])[C:27]([F:35])([F:36])[C:28]([F:33])([F:34])[C:29]([F:32])([F:31])[F:30])=[O:22])[CH3:58]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57041336N,N-DimethylaminoethylamineHCID 58090242Bis(3,3,4,4,5,5,6,6,6-nonafluorohexyl) butanedioate

Product 1

HCID 226306862-[2-(Dimethylamino)ethylamino]succinic acid bis(3,3,4,4,5,5,6,6,6-nonafluorohexyl) esterYield 79%

Procedure

1,4-di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) succinate (500 g, 0.82 mol), N,N-dimethylaminoethylamine (79.5 g, 0.90 mol) and potassium carbonate (11.3 g, 0.08 mol) were dissolved in acetonitrile (500 mL) and refluxed with heating for 45 minutes. Then, the reaction mixture was transferred to a separating funnel and added with ethyl acetate (2 L). The organic phase was washed with an aqueous solution of sodium chloride (1.5 L) and collected, and the organic solvent was evaporated under reduced pressure to obtain the target compound (453 g, yield: 79%) as light yellow oil.

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 45 minutes
  3. customThen, the reaction mixture was transferred to a separating funnel
  4. washThe organic phase was washed with an aqueous solution of sodium chloride (1.5 L)
  5. customcollected
  6. customthe organic solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fcb377b6288b41fc9068bfa41747b645
Source dataset
uspto-grants-2005_03
Patent number
US06872515B2

Reaction notes

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