Sodium hydride → alpha-(11-Bromoundecyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrile

HRID 863870Notes

Reaction equation

HRID 863870 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]Br>O1CCCC1>[Br:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:11]([S:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:12]#[N:13]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 855511,11-DibromoundecaneHCID 105421673,4-Dimethoxy-alpha[(4-methylphenyl)thio]benzeneacetonitrile

Product 1

HCID 10673824alpha-(11-Bromoundecyl)-3,4-dimethoxy-alpha-[(4-methylphenyl)thio]benzeneacetonitrileYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.50 g of 3,4-dimethoxy-α-[(4-methylphenyl)thio]benzeneacetonitrile in 50 mL of tetrahydrofuran, under an argon atmosphere with stirring, is added 0.367 g of 60% sodium hydride in oil. After 1.5 hours, 10.0 g of 1,11-dibromoundecane is added and stirring is continued for 43 hours. The reaction mixture is evaporated and the residue partitioned between diethyl ether and water. The organic phase is separated, washed with water, dried with magnesium sulfate, filtered and evaporated leaving an oil. The oil is purified via column chromatography, using hexane/ether (1:1) to afford 3.25 g of the desired product as a colorless oil. MS(CI): m/z 532(MH+). Calcd for C32H39NO6S: C=63.15, H=7.19, N=2.63, Br=15.00, S=6.02 Found C=63.12, H=7.17, N=2.52, Br=14.77, S=6.02

Workup

  1. waitis continued for 43 hours
  2. customThe reaction mixture is evaporated
  3. customthe residue partitioned between diethyl ether and water
  4. customThe organic phase is separated
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customleaving an oil
  10. customThe oil is purified via column chromatography

Sources & evidence

ORD record
ord-588f19b6ae7e41fb979b42ad19177077
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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