N,N,N',N'-Tetramethylethylenediamine → HCID 87573187, compound

HRID 747647Notes

Reaction equation

HRID 747647 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[S:16]([O-:19])(=[O:18])=[O:17])([CH3:3])[CH3:2].[OH:20][C:21]1[CH:26]=[CH:25][C:24]([S+:27]([C:38]2[CH:43]=[CH:42][C:41]([C:44]([CH3:47])([CH3:46])[CH3:45])=[CH:40][CH:39]=2)[C:28]2[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1.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>[CH:13]([C:6]1[CH:7]=[C:8]([CH:10]([CH3:11])[CH3:12])[CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[S:16]([O-:19])(=[O:17])=[O:18])([CH3:14])[CH3:15].[CH:62]([O:64][CH2:65][CH2:66][O:20][C:21]1[CH:26]=[CH:25][C:24]([S+:27]([C:38]2[CH:39]=[CH:40][C:41]([C:44]([CH3:47])([CH3:46])[CH3:45])=[CH:42][CH:43]=2)[C:28]2[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=2)=[CH:23][CH:22]=1)=[CH2:63]

Participants

6

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 80742-Chloroethyl vinyl etherHCID 11430Potassium CarbonateHCID 87573349HCID 87573349, compound

Product 1

HCID 87573187HCID 87573187, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

4-Hydroxyphenyldi(4-t-butylphenyl)sulfonium 2,4,6-triisopropylbenzenesulfonate salt (5.00 g), potassium carbonate (1.28 g), and N,N,N′,N′-tetramethylethylenediamine (0.10 g) were dissolved in dimethyl sulfoxide (15 g). Chloroethyl vinyl ether (0.83 g) was added to the solution, followed by heating to 80° C. The reaction mixture was stirred for 15 hours and cooled to 30° C. or lower. After removal of solid through filtration, water (75 g) and dichloromethane (44 g) were added to the filtrate, 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 4.64 g of a brown oily substance. Through 1H-NMR and ion chromatography, the substance was identified to be 4-vinyloxyethoxyphenyldi(4-t-butylphenyl)sulfonium 2,4,6-triisopropylbenzenesulfonate salt.

Workup

  1. temperaturecooled to 30° C.
  2. customAfter removal of solid
  3. filtrationthrough filtration, water (75 g) and dichloromethane (44 g)
  4. additionwere added to the filtrate, whereby the target substance
  5. extractionwas extracted to 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-bac3529512924a2985adbba78e74fd05
Source dataset
uspto-grants-2008_07
Patent number
US07396960B2

Reaction notes

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