3-Anilinopropionitrile → alpha-(Anilinomethylene)-3,5-bis(dimethylamino)-4-methoxyhydrocinnamonitrile

HRID 441303Notes

Reaction equation

HRID 441303 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1[CH:4]=[C:5]([CH:13]=[C:14]([N:18]([CH3:20])[CH3:19])[C:15]=1[O:16][CH3:17])[CH:6](O)CS(C)(=O)=O.C[O-].[Na+].[NH:25]([CH2:32][CH2:33][C:34]#[N:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CS(C)=O>[NH:25]([CH:32]=[C:33]([CH2:6][C:5]1[CH:13]=[C:14]([N:18]([CH3:19])[CH3:20])[C:15]([O:16][CH3:17])=[C:3]([N:2]([CH3:21])[CH3:1])[CH:4]=1)[C:34]#[N:35])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 544065843,5-Bis(dimethylamino)-4-methoxy-alpha-[(methylsulfonyl)methyl]benzyl alcohol

Product 1

HCID 70571882alpha-(Anilinomethylene)-3,5-bis(dimethylamino)-4-methoxyhydrocinnamonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 9.76 g. of 3,5-bis(dimethylamino)-4-methoxy-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 poured into 250 ml. of water, the precipitated oil extracted with ethyl acetate, the ethyl acetate solution dried over sodium sulfate and evaporated. By recrystallization of the residue from high-boiling petroleum ether, there was obtained α-(anilinomethylene)-3,5-bis(dimethylamino)-4-methoxyhydrocinnamonitrile, having a melting point of 103°-105° C.

Workup

  1. additionA mixture of 9.76 g
  2. additionThe mixture was poured into 250 ml
  3. extractionof water, the precipitated oil extracted with ethyl acetate
  4. dry with materialthe ethyl acetate solution dried over sodium sulfate
  5. customevaporated
  6. customBy recrystallization of the residue from high-boiling petroleum ether

Sources & evidence

ORD record
ord-2b2625afe5c94a8cae91687fb3c2ee91
Source dataset
uspto-grants-1977_08
Patent number
US04039543

Reaction notes

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