3-Anilinopropionitrile → alpha-(Anilinomethyl)-3,4,5-tris(dimethylamino)hydrocinnamonitrile

HRID 441316Notes

Reaction equation

HRID 441316 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([N:19]([CH3:21])[CH3:20])[C:15]=1[N:16]([CH3:18])[CH3:17])[CH:6](O)CS(C)(=O)=O.C[O-].[Na+].[NH:26]([CH2:33][CH2:34][C:35]#[N:36])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CS(C)=O>[NH:26]([CH2:33][CH:34]([CH2:6][C:5]1[CH:13]=[C:14]([N:19]([CH3:20])[CH3:21])[C:15]([N:16]([CH3:18])[CH3:17])=[C:3]([N:2]([CH3:1])[CH3:22])[CH:4]=1)[C:35]#[N:36])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 539878893,4,5-Tris(dimethylamino)-alpha-[(methylsulfonyl)methyl]benzyl alcohol

Product 1

HCID 54380707alpha-(Anilinomethyl)-3,4,5-tris(dimethylamino)hydrocinnamonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 8.96 g. of 3,4,5-tris(dimethylamino)-α-[(methylsulfonyl)methyl]benzyl alcohol, 2.56 g. of sodium methylate and 6.6 g. of β-anilinopropionitrile in 70 ml. of dimethylsulfoxide was stirred at room temperature under nitrogen for 50 minutes. The mixture was poured into 500 ml. of ice water, the separated oil extracted with ethyl acetate, the ethyl acetate solution dried over sodium sulfate and evaporated. By purification of the residue over aluminum oxide with benzene and recrystallization from ethanol, there was obtained α-(anilinomethyl)-3,4,5-tris(dimethylamino)hydrocinnamonitrile having a melting point of 179°-181° C.

Workup

  1. additionA mixture of 8.96 g
  2. additionThe mixture was poured into 500 ml
  3. extractionof ice water, the separated oil extracted with ethyl acetate
  4. dry with materialthe ethyl acetate solution dried over sodium sulfate
  5. customevaporated
  6. customBy purification of the residue over aluminum oxide
  7. customwith benzene and recrystallization from ethanol

Sources & evidence

ORD record
ord-26ce5d183528471b992f1b3d8b9d2618
Source dataset
uspto-grants-1977_08
Patent number
US04039543

Reaction notes

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