3-Anilinopropionitrile → 4'-(3-anilino-2-cyanoallyl)-2',6'-bis(dimethylamino)-N-methylacetanilide

HRID 441323Notes

Reaction equation

HRID 441323 reaction equation
C[O-].[Na+].[CH3:4][N:5]([CH3:27])[C:6]1[CH:16]=[C:15]([CH:17](O)CS(C)(=O)=O)[CH:14]=[C:13]([N:24]([CH3:26])[CH3:25])[C:7]=1[N:8]([CH3:12])[C:9](=[O:11])[CH3:10].[NH:28]([CH2:35][CH2:36][C:37]#[N:38])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CS(C)=O>[NH:28]([CH:35]=[C:36]([C:37]#[N:38])[CH2:17][C:15]1[CH:14]=[C:13]([N:24]([CH3:26])[CH3:25])[C:7]([N:8]([CH3:12])[C:9](=[O:11])[CH3:10])=[C:6]([N:5]([CH3:27])[CH3:4])[CH:16]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 202904332',6'-bis(dimethylamino)-4'-[1-hydroxy-2-(methylsulfonyl)ethyl]-N-methylacetanilide

Product 1

HCID 705701704'-(3-anilino-2-cyanoallyl)-2',6'-bis(dimethylamino)-N-methylacetanilide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1.23 g. of sodium methylate, 5.31 g. of 2',6'-bis(dimethylamino)-4'-[1-hydroxy-2-(methylsulfonyl)ethyl]N-methylacetanilide and 3.3 g. of β-anilinopropionitrile in 40 ml. of dimethylsulfoxide was stirred at room temperature under nitrogen for 5 hours. 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 evaporated. After purification of the residue over aluminum oxide with benzene and recrystallization from ethyl acetate/petroleum ether, there was obtained 4'-(3-anilino-2-cyanoallyl)-2',6'-bis(dimethylamino)-N-methylacetanilide having a melting point of 190°-200° C.

Workup

  1. additionA mixture of 1.23 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. customAfter purification of the residue over aluminum oxide
  7. customwith benzene and recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-e331399037fb43cebd11cdf8c35c013e
Source dataset
uspto-grants-1977_08
Patent number
US04039543

Reaction notes

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