N,N,N',N'-Tetramethylethylenediamine → HCID 178467770, compound

HRID 747646Notes

Reaction equation

HRID 747646 reaction equation
[F:1][C:2]([F:17])([S:13]([O-:16])(=[O:15])=[O:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].O[C:19]1[CH:24]=[CH:23][C:22]([S+:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:21][CH:20]=1.[C:38](=[O:41])([O-])[O-].[K+].[K+].CN(C)[CH2:46][CH2:47]N(C)C.[CH:52]([O:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59]CCCCl)=[CH2:53]>CS(C)=O>[F:17][C:2]([F:1])([S:13]([O-:16])(=[O:15])=[O:14])[C:3]([F:11])([F:12])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].[CH:52]([O:54][CH:55]([CH2:56][CH2:57][CH2:58][CH3:59])[CH2:46][CH2:47][CH2:38][O:41][SH+:25]([C:22]1[CH:21]=[CH:20][CH:19]=[CH:24][CH:23]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[CH2:53]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 11430Potassium CarbonateHCID 22481373HCID 22481373, compoundHCID 566088708-Chlorooctyl vinyl ether

Product 1

HCID 178467770HCID 178467770, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

4-Hydroxyphenyldiphenylsulfonium perfluorobutanesulfonate salt (2.67 g), potassium carbonate (0.78 g), and N,N,N′,N′-tetramethylethylenediamine (0.05 g) were dissolved in dimethyl sulfoxide (13.3 g). 8-Chlorooctyl vinyl ether (1.05 g) was added to the solution, followed by heating to 80° C. The reaction mixture was stirred for 18 hours and cooled to 30° C. or lower. After removal of solid through filtration, water (13.3 g) was added to the filtrate, and the aqueous layer was washed three times with hexane (7.96 g). To the washed aqueous layer, dichloromethane (10.6 g) and water (14 g) were added under stirring, whereby the target substance was extracted to the dichloromethane layer. The organic layer was repeatedly washed with distilled water until the pH of the separated aqueous layer was shifted to 7. The solvent was removed by means of a rotary evaporator, to thereby yield 2.53 g of a brown oily substance. Through 1H-NMR and ion chromatography, the substance was identified to be 4-vinyloxyoctoxyphenyldiphenylsulfonium perfluorobutanesulfonate salt.

Workup

  1. temperaturecooled to 30° C.
  2. customAfter removal of solid
  3. filtrationthrough filtration, water (13.3 g)
  4. additionwas added to the filtrate
  5. washthe aqueous layer was washed three times with hexane (7.96 g)
  6. additionTo the washed aqueous layer, dichloromethane (10.6 g) and water (14 g) were added
  7. stirringunder stirring
  8. extractionwhereby the target substance was extracted to the dichloromethane layer
  9. washThe organic layer was repeatedly washed with distilled water until the pH of the separated aqueous layer
  10. customThe solvent was removed by means of a rotary evaporator

Sources & evidence

ORD record
ord-e35ad0baf853479d806cf6fed2e05572
Source dataset
uspto-grants-2008_07
Patent number
US07396960B2

Reaction notes

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