N,N,N',N'-Tetramethylethylenediamine → HCID 87572956, compound

HRID 2265790Notes

Reaction equation

HRID 2265790 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O-:12])(=[O:11])=[O:10].[OH:15][C:16]1[CH:21]=[CH:20][C:19]([S+:22]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:35][CH:34]=2)[C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)CCN(C)C.[CH:57]([O:59][CH2:60][CH2:61]Cl)=[CH2:58]>CS(C)=O>[F:14][C:2]([F:1])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O-:12])(=[O:11])=[O:10].[CH:57]([O:59][CH2:60][CH2:61][O:15][C:16]1[CH:21]=[CH:20][C:19]([S+:22]([C:33]2[CH:34]=[CH:35][C:36]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:37][CH:38]=2)[C:23]2[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1)=[CH2:58]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 80742-Chloroethyl vinyl etherHCID 11430Potassium CarbonateHCID 87574721HCID 87574721, compound

Product 1

HCID 87572956HCID 87572956, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

4-Hydroxyphenyldi(4-t-butylphenyl)sulfonium 2-trifluoromethylbenzenesulfonate (4.51 g), potassium carbonate (5.30 g), and N,N,N′,N′-tetramethylethylenediamine (0.53 g) were dissolved in dimethyl sulfoxide (30 g). Subsequently, chloroethyl vinyl ether (10.03 g) was added to the resultant solution, followed by heating to 80° C. and stirring for 15 hours. The resultant reaction mixture was cooled to 30° C. or lower. After removal of solid matter through filtration, water (150 g) and dichloromethane (93 g) were added to the filtrate 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 8.57 g of a red powdery substance. Through 1H-NMR analysis and ion chromatography, this substance was identified to be 4-vinyloxyethoxyphenyldi(4-t-butylphenyl)sulfonium 2-trifluoromethylbenzenesulfonate.

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas cooled to 30° C.
  3. customAfter removal of solid matter
  4. filtrationthrough filtration, water (150 g) and dichloromethane (93 g)
  5. additionwere added to the filtrate for extraction of a target substance into the dichloromethane layer
  6. washThe organic layer was repeatedly washed with distilled water until the pH of the separated aqueous layer
  7. customThe solvent was removed by means of a rotary evaporator

Sources & evidence

ORD record
ord-d2d9fcfcee434bbbbddd6a8295316cbd
Source dataset
uspto-grants-2010_12
Patent number
US07858287B2

Reaction notes

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