N,N,N',N'-Tetramethylethylenediamine → HCID 87574591, compound

HRID 2265785Notes

Reaction equation

HRID 2265785 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:37]2[CH:42]=[CH:41][C:40]([C:43]([CH3:46])([CH3:45])[CH3:44])=[CH:39][CH:38]=2)[C:27]2[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=2)=[CH:21][C:20]=1[CH3:47].C(=O)([O-])[O-].[K+].[K+].CN(C)CCN(C)C.[CH:62]([O:64][CH2:65][CH2:66]Cl)=[CH2:63]>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:62]([O:64][CH2:65][CH2:66][O:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([S+:26]([C:27]2[CH:28]=[CH:29][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:31][CH:32]=2)[C:37]2[CH:42]=[CH:41][C:40]([C:43]([CH3:46])([CH3:45])[CH3:44])=[CH:39][CH:38]=2)=[CH:21][C:20]=1[CH3:47])=[CH2:63]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 80742-Chloroethyl vinyl etherHCID 11430Potassium CarbonateHCID 87573325HCID 87573325, compound

Product 1

HCID 87574591HCID 87574591, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

4-Hydroxy-3,5-dimethylphenyldi(4-t-butylphenyl)sulfonium perfluorobutanesulfonate (28.6 g), potassium carbonate (8.10 g), and N,N,N′,N′-tetramethylethylenediamine (0.46 g) were dissolved in dimethyl sulfoxide (142 g). Subsequently, chloroethyl vinyl ether (6.08 g) was added to the resultant solution, followed by heating to 80° C. and stirring for 19 hours. The resultant reaction mixture was cooled to 30° C. or lower. After removal of solid matter through filtration, water (20.9 g) was added to the filtrate, and the aqueous layer was washed thrice with hexane (85.1 g). Dichloromethane (226 g) and water (141 g) were added to the washed aqueous layer, followed by stirring for extraction of a target substance into the dichloromethane layer. The organic layer was repeatedly washed with distilled water until the pH of the separated aqueous layer became 7. The solvent was removed by means of a rotary evaporator, to thereby yield 27.4 g of a brown oily substance. Through 1H-NMR analysis and ion chromatography, this substance was identified to be 4-vinyloxyethoxy-3,5-dimethylphenyldi(4-t-butylphenyl)sulfonium perfluorobutanesulfonate.

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas cooled to 30° C.
  3. customAfter removal of solid matter
  4. filtrationthrough filtration, water (20.9 g)
  5. additionwas added to the filtrate
  6. washthe aqueous layer was washed thrice with hexane (85.1 g)
  7. additionDichloromethane (226 g) and water (141 g) were added to the washed aqueous layer
  8. stirringby stirring for extraction of a target substance into 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-09830a89d38d4717acf9f211790ae3d3
Source dataset
uspto-grants-2010_12
Patent number
US07858287B2

Reaction notes

Loading…