1,2-Dimethoxyethane → 4-{2-[4-(Methanesulfonyl)phenyl]ethenyl}-N,N-dimethylaniline

HRID 414432Notes

Reaction equation

HRID 414432 reaction equation
[H-].[Na+].[CH3:3][N:4]([C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1C=O)[CH3:5].[CH3:14][S:15]([C:18]1[CH:32]=[CH:31][C:21]([CH2:22]P(=O)(OCC)OCC)=[CH:20][CH:19]=1)(=[O:17])=[O:16].[CH3:33]OCCOC>>[CH3:5][N:4]([CH3:3])[C:6]1[CH:7]=[CH:10][C:11]([CH:33]=[CH:22][C:21]2[CH:20]=[CH:19][C:18]([S:15]([CH3:14])(=[O:16])=[O:17])=[CH:32][CH:31]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 34289Benzaldehyde, (dimethylamino)-HCID 14419480(4-Methanesulfonylbenzyl)phosphonic acid diethyl ester

Product 1

HCID 537801194-{2-[4-(Methanesulfonyl)phenyl]ethenyl}-N,N-dimethylanilineYield 66%

Procedure

To a solution of 2.8 g (0.07 mol) of 60% sodium hydride dispersion, 7.46 g (0.05 mole) N,N-dimethylaminobenzaldehyde, and 100 mL of dry, freshly distilled 1,2-dimethoxyethane (DME) under nitrogen, at room temperature, was added 15.3 g (0.05 mole) diethyl 4-methylsulfonylbenzylphosphonate with vigorous stirring. The mixture immediately turned bright yellow. The mixture was heated at reflux for 2 hours. After cooling the very bright yellow solution was poured over 300 g of crushed ice under nitrogen blanket. The bright yellow solid was collected by filtration, washed with water, and air dried. Recrystallization from a 1:1 mixture of absolute ethanol and dry pyridine yielded 9.97 g (66%) of bright yellow crystals mp 242°-243° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling the very bright yellow solution
  4. filtrationThe bright yellow solid was collected by filtration
  5. washwashed with water, and air
  6. customdried
  7. customRecrystallization
  8. additionfrom a 1:1 mixture of absolute ethanol and dry pyridine

Sources & evidence

ORD record
ord-bd7864e85ae146d5ada7d2e9e68ab8da
Source dataset
uspto-grants-1988_12
Patent number
US04792208

Reaction notes

Loading…