3-Anilinopropionitrile → HCID 70572878, compound

HRID 441308Notes

Reaction equation

HRID 441308 reaction equation
[CH3:1][O:2][C:3]1[C:15]([N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)=[CH:14][C:6]([CH:7](O)CS(C)(=O)=O)=[CH:5][C:4]=1[N:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.C[O-].[Na+].[NH:29]([CH2:36][CH2:37][C:38]#[N:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CS(C)=O>[NH:29]([CH:36]=[C:37]([CH2:7][C:6]1[CH:5]=[C:4]([N:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)[C:3]([O:2][CH3:1])=[C:15]([N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)[CH:14]=1)[C:38]#[N:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 53651919HCID 53651919, compound

Product 1

HCID 70572878HCID 70572878, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1.8 g. of 4-methoxy- α -[(methylsulfonyl)methyl]-3,5-di-(pyrrol-1-yl)benzyl alcohol, 0.41 g. of sodium methylate and 1.1 g. of β-anilinopropionitrile in 12 ml. of dimethylsulfoxide was stirred with the exclusion of moisture for 3 hours at room temperature. The mixture was diluted with 100 ml. of water, the precipitated oil extracted with ethyl acetate, the ethyl acetate solution dried over sodium sulfate and evaporated. By purification of the residue over aluminum oxide with benzene and recrystallization from ethyl acetate/petroleum ether, there was obtained α -(anilinomethylene)-4-methoxy-3,5-di(pyrrol-1-yl)hydrocinnamonitrile, having a melting point of 152° C.

Workup

  1. additionA mixture of 1.8 g
  2. additionThe mixture was diluted with 100 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 purification of the residue over aluminum oxide
  7. customwith benzene and recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-335acc99f0e04f01b457b2ac7a3d7746
Source dataset
uspto-grants-1977_08
Patent number
US04039543

Reaction notes

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