N,N,N',N'-Tetramethylethylenediamine → HCID 87781844, compound

HRID 747643Notes

Reaction equation

HRID 747643 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].[OH:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([S+:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:21][C:20]=1[CH3:39].C(=O)([O-])[O-].[K+].[K+].CN(C)CCN(C)C.[CH:54]([O:56][CH2:57][CH2:58]Cl)=[CH2:55]>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:54]([O:56][CH2:57][CH2:58][O:18][C:19]1[C:20]([CH3:39])=[CH:21][C:22]([S+:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:23][C:24]=1[CH3:25])=[CH2:55]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 80742-Chloroethyl vinyl etherHCID 11430Potassium CarbonateHCID 22625480HCID 22625480, compound

Product 1

HCID 87781844HCID 87781844, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

4-Hydroxy-3,5-dimethylphenyldiphenylsulfonium perfluorobutanesulfonate salt (56.1 g), potassium carbonate (18.4 g), and N,N,N′,N′-tetramethylethylenediamine (1.07 g) were dissolved in dimethyl sulfoxide (118 g). Chloroethyl vinyl ether (14.2 g) was added to the solution, followed by heating to 80° C. The reaction mixture was stirred for 47 hours and cooled to 30° C. or lower. After removal of solid through filtration, water (280 g) was added to the filtrate, and the aqueous layer was washed three times with hexane (168 g). To the washed aqueous layer, dichloromethane (226 g) and water (50 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 41.0 g of an oily substance. Through 1H-NMR and ion chromatography, the substance was identified to be 4-vinyloxyethoxy-3,5-dimethylphenyldiphenylsulfonium perfluorobutanesulfonate salt.

Workup

  1. temperaturecooled to 30° C.
  2. customAfter removal of solid
  3. filtrationthrough filtration, water (280 g)
  4. additionwas added to the filtrate
  5. washthe aqueous layer was washed three times with hexane (168 g)
  6. additionTo the washed aqueous layer, dichloromethane (226 g) and water (50 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-2c450bb9fb84496d881b6bba2156bc68
Source dataset
uspto-grants-2008_07
Patent number
US07396960B2

Reaction notes

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