3-Anilinopropionitrile → HCID 70569388, compound

HRID 1413736Notes

Reaction equation

HRID 1413736 reaction equation
[Cl:1][C:2]1[C:14]([NH:15][CH3:16])=[CH:13][C:5]([CH:6](O)CS(C)(=O)=O)=[CH:4][C:3]=1[N:17]([CH3:19])[CH3:18].C[O-].[Na+].[NH:23]([CH2:30][CH2:31][C:32]#[N:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CS(C)=O>[NH:23]([CH:30]=[C:31]([CH2:6][C:5]1[CH:13]=[C:14]([NH:15][CH3:16])[C:2]([Cl:1])=[C:3]([N:17]([CH3:19])[CH3:18])[CH:4]=1)[C:32]#[N:33])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 54205600HCID 54205600, compound

Product 1

HCID 70569388HCID 70569388, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 9.48 g. of 4-chloro-3-dimethylamino-5-methylamino-α-[(methylsulfonyl)methyl]benzyl alcohol, 1.8 g. of sodium methylate and 4.8 g. of β-anilinopropionitrile in 20 ml. of dimethylsulfoxide was stirred with the exclusion of moisture for 5 hours at 50° C. The mixture was cooled, poured into 200 ml. of water, the precipitated oil extracted with ethyl acetate, the ethyl acetate solution dried over sodium sulfate and evaporated. By purification of the product over aluminum oxide with benzene and recrystallization from ethanol, there was obtained α-(anilinomethylene)-4-chloro-3-dimethylamino-5-methylaminohydrocinnamonitrile, having a melting point of 173°-174° C.

Workup

  1. additionA mixture of 9.48 g
  2. temperatureThe mixture was cooled
  3. additionpoured into 200 ml
  4. extractionof water, the precipitated oil extracted with ethyl acetate
  5. dry with materialthe ethyl acetate solution dried over sodium sulfate
  6. customevaporated
  7. customBy purification of the product over aluminum oxide
  8. customwith benzene and recrystallization from ethanol

Sources & evidence

ORD record
ord-dd692e4d5eb743fcafb48e0d613cf6aa
Source dataset
uspto-grants-1981_02
Patent number
US04251454

Reaction notes

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