N,N-Dimethylaniline → HCID 18965748, compound

HRID 2226638Notes

Reaction equation

HRID 2226638 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH2:16]([C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH3:38][N:39]([CH3:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCOCC1>[CH2:16]([C:28]1[CH:33]=[CH:32][C:31]([S:34]([O-:36])(=[O:7])=[O:35])=[CH:30][CH:29]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N+:39]([CH3:46])([CH3:38])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 115054-Methylbenzyl alcoholHCID 1042154-Dodecylbenzenesulfonyl chlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 18965748HCID 18965748, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

12.21 g (0.1 mol) of 4-methylbenzylalcohol was dissolved in 60 g of 1,4-dioxane, and was added while cooling to 11.22 g (0.1 mol) of potassium t-butoxide. The solution was added dropwise to a solution of 34.5 g (0.1 mol) of 4-dodecylbenzenesulfonyl chloride in 1,4-dioxane over one hour. Subsequently, 12.12 g (0.1 mol) of N,N-dimethylaniline was added and stirred at room temperature for 16 hours. After the completion of the reaction, the mixture was filtered and concentrated, and the precipitated solid was washed with ether and dried to give the titled compound. Yield: 53%.

Workup

  1. additionwas added
  2. customAfter the completion of the reaction
  3. filtrationthe mixture was filtered
  4. concentrationconcentrated
  5. washthe precipitated solid was washed with ether
  6. customdried

Sources & evidence

ORD record
ord-152854a4ed8d452baffab9c49ceeafac
Source dataset
uspto-grants-1994_09
Patent number
US05349067

Reaction notes

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