3-Anilinopropionitrile → HCID 70570292, compound

HRID 1413735Notes

Reaction equation

HRID 1413735 reaction equation
[Cl:1][C:2]1[C:14]([N:15]([CH3:17])[CH3:16])=[CH:13][C:5]([CH:6](O)CS(C)(=O)=O)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19].C[O-].[Na+].[NH:24]([CH2:31][CH2:32][C:33]#[N:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CS(C)=O>[NH:24]([CH:31]=[C:32]([CH2:6][C:5]1[CH:13]=[C:14]([N:15]([CH3:16])[CH3:17])[C:2]([Cl:1])=[C:3]([N:18]([CH3:19])[CH3:20])[CH:4]=1)[C:33]#[N:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 54553521HCID 54553521, compound

Product 1

HCID 70570292HCID 70570292, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 15.7 g. of 4-chloro-3,5-bis(dimethylamino)-α-[(methylsulfonyl)methyl]benzyl alcohol, 2.8 g. of sodium methylate and 7.1 g. of β-anilinopropionitrile in 31 ml. of dimethylsulfoxide was stirred with the exclusion of moisture for 5 hours at 50° C. The mixture was poured into 200 ml. of water, the precipitated oil extracted with ethyl acetate, the ethyl acetate solution dried over sodium sulfate and evaporated in vacuo. By purification of the residue over aluminum oxide with benzene and recrystallization from ethyl acetate/petroleum ether, there was obtained α-(anilinomethylene)-4-chloro-3,5-bis(dimethylamino)hydrocinnamonitrile, having a melting point of 168° C.

Workup

  1. additionA mixture of 15.7 g
  2. additionThe mixture was poured into 200 ml
  3. extractionof water, the precipitated oil extracted with ethyl acetate
  4. dry with materialthe ethyl acetate solution dried over sodium sulfate
  5. customevaporated in vacuo
  6. customBy purification of the residue over aluminum oxide
  7. customwith benzene and recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-926d4c524c7d4ee699671f4f521e2350
Source dataset
uspto-grants-1981_02
Patent number
US04251454

Reaction notes

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