Chloroform → 1,4-di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) 2-(N,N-dimethylaminoethanethionyl)maleate

HRID 352714Notes

Reaction equation

HRID 352714 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])/[CH:2]=[CH: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].Cl.CN([CH:43]([SH:45])C)C.C(=O)([O-])[O-].[K+].[K+].C(Cl)(Cl)Cl.[CH3:56][N:57]([CH3:60])[CH:58]=O>>[CH3:56][N:57]([CH2:58][C:43](/[C:2](=[CH: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])=[S:45])[CH3:60]

Participants

6

Reactant 5

HCID 6212ChloroformHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 22036395N,N-dimethylaminoethanethiol hydrochlorideHCID 867598121,4-Di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) maleate

Product 1

HCID 867598111,4-di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) 2-(N,N-dimethylaminoethanethionyl)maleateYield 54%

Conditions

Temperature
60 °C

Procedure

In an amount of 25.1 g (41 mmol) of 1,4-di(3,3,4,4,5,5,6,6,6-nonafluorohexyl) maleate, 6.4 g (45 mmol) of N,N-dimethylaminoethanethiol hydrochloride and 5.7 g (41 mmol) of potassium carbonate were dissolved in 60 mL of N,N-dimethylformamide and stirred at 60° C. for 4 hours. Then, the reaction mixture was added with 500 mL of chloroform and the organic phase was washed with a saturated aqueous sodium hydrogencarbonate solution. Subsequently, the organic layer was collected, and the organic solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:2 to 0:10 (volume ratio)) to obtain 15.8 g (yield: 54%) of the target compound.

Workup

  1. washthe organic phase was washed with a saturated aqueous sodium hydrogencarbonate solution
  2. customSubsequently, the organic layer was collected
  3. customthe organic solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:2 to 0:10 (volume ratio))

Sources & evidence

ORD record
ord-0ca776c3fc764bed951222c2f42aaf46
Source dataset
uspto-grants-2004_06
Patent number
US06747169B2

Reaction notes

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