3-Anilinopropionitrile → HCID 86734980, compound

HRID 1413748Notes

Reaction equation

HRID 1413748 reaction equation
[C:1]([C:5]1[C:17]([N:18]([CH3:20])[CH3:19])=[CH:16][C:8]([CH:9](O)CS(C)(=O)=O)=[CH:7][C:6]=1[N:21]([CH3:23])[CH3:22])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].[NH:27]([CH2:34][CH2:35][C:36]#[N:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CS(C)=O>[NH:27]([CH:34]=[C:35]([CH2:9][C:8]1[CH:7]=[C:6]([N:21]([CH3:23])[CH3:22])[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[C:17]([N:18]([CH3:19])[CH3:20])[CH:16]=1)[C:36]#[N:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 86734981HCID 86734981, compound

Product 1

HCID 86734980HCID 86734980, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4.66 g. of 4-tert. butyl-3,5-bis(dimethylamino)-α-[(methylsulfonyl)methyl]benzyl alcohol, 1.28 g. of sodium methylate and 3.3 g. of β-anilinopropionitrile in 35 ml. of dimethylsulfoxide was stirred at room temperature under nitrogen for 60 minutes. The mixture was poured into 200 ml. of ice water, the separated oil extracted with ethyl acetate, the ethyl acetate solution dried over sodium sulfate and then evaporated. By purification of the residue over aluminum oxide with benzene and recrystallization from ethanol, there was obtained α-(anilinomethylene)-4-tert. butyl-3,5-bis(dimethylamino)hydrocinnamonitrile having a melting point of 150° C.

Workup

  1. additionA mixture of 4.66 g
  2. additionThe mixture was poured into 200 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-7f9c042bb24544599d9eb9682b106321
Source dataset
uspto-grants-1981_02
Patent number
US04251454

Reaction notes

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