Benzene → 4-Dibutylamino-beta,beta-di(methylsulfonyl)styrene

HRID 1655109Notes

Reaction equation

HRID 1655109 reaction equation
[CH2:1]([N:5]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:18][S:19]([CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])(=[O:21])=[O:20].N1C=CC=CC=1.C1C=CC=CC=1>N1CCCCC1.O>[CH2:1]([N:5]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[C:22]([S:23]([CH3:26])(=[O:25])=[O:24])[S:19]([CH3:18])(=[O:21])=[O:20])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 241BenzeneHCID 1049PyridineHCID 240586di(methylsulfonyl)methaneHCID 6053914-(Dibutylamino)benzaldehyde

Product 1

HCID 200776804-Dibutylamino-beta,beta-di(methylsulfonyl)styreneYield 46.4%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 962WaterSolvent

Procedure

A mixture of 23.3 g (0.10 mol) of 4-dibutylaminobenzaldehyde, 17 g (0.10 mol) of di(methylsulfonyl)methane, 15 mL of pyridine, 7 drops of piperidine, and 400 mL of benzene was heated at reflux for 18 hr, with continuous azeotropic separation of the water evolved. Approximately half of the benzene was removed by distillation, and 200 mL of heptane was added. Upon cooling to room temperature, a white precipitate formed. The crude product was purified by silica gel chromatography followed by micrystallization from ethanol, from toluene, and from methanol, producing 18 g (46%) of (2). A sample of (2) that was sublimed in vacuo melted at 114.5°-115° C.

Workup

  1. temperaturewas heated
  2. customApproximately half of the benzene was removed by distillation, and 200 mL of heptane
  3. additionwas added
  4. customa white precipitate formed
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-32ef17802b9b4f67a4870fddf35793eb
Source dataset
uspto-grants-1995_04
Patent number
US05410630

Reaction notes

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