Sodium hydride → 4-Dioctadecylamino-4'-methylsulfonylstilbene

HRID 414444Notes

Reaction equation

HRID 414444 reaction equation
[H-].[Na+].C([N:21]([C:40]1[CH:47]=[CH:46][CH:45]=[CH:44][C:41]=1[CH:42]=O)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])CCCCCCCCCCCCCCCCC.[CH3:48][S:49]([C:52]1[CH:66]=[CH:65][C:55]([CH2:56]P(=O)(OCC)OCC)=[CH:54][CH:53]=1)(=[O:51])=[O:50]>COCCOC>[CH2:22]([N:21]([CH2:40][CH2:47][CH2:46][CH2:45][CH2:44][CH2:41][CH2:42][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH3:22])[C:46]1[CH:47]=[CH:40][C:41]([CH:42]=[CH:56][C:55]2[CH:54]=[CH:53][C:52]([S:49]([CH3:48])(=[O:50])=[O:51])=[CH:66][CH:65]=2)=[CH:44][CH:45]=1)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 14419480(4-Methanesulfonylbenzyl)phosphonic acid diethyl esterHCID 53874326N,N-dioctadecylaminobenzaldehyde

Product 1

HCID 543842614-Dioctadecylamino-4'-methylsulfonylstilbeneYield 101.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of 420 mG of 60% sodium hydride dispersion (0.011 mol), 6.26 g (0.01 mol) of N,N-dioctadecylaminobenzaldehyde and 40 mL of dry, freshly distilled 1,2-dimethoxyethane (DME) under nitrogen, at room temperature, with vigorous stirring, was added a solution of 3.06 g (0.01 mol) of diethyl 4-methylsulfonylbenzylphosphonate in 10 mL 1,2-dimethoxyethane. The mixture immediately turned bright yellow. The reaction mixture was heated at reflux for 2 hours. After cooling, the bright yellow solution was poured over 100 g of crushed ice under a nitrogen blanket. The bright yellow solid was collected by filtration, washed with cold water, and air dried. Recrystallization from ethanol yielded 3.95 g (50.7%) of bright yellow powder mp 75°-76° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling
  4. filtrationThe bright yellow solid was collected by filtration
  5. washwashed with cold water, and air
  6. customdried
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-2f19695ca7c34f869c975b36192b5c87
Source dataset
uspto-grants-1988_12
Patent number
US04792208

Reaction notes

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