3-Anilinopropionitrile → HCID 70572878, compound

HRID 1413739Notes

Reaction equation

HRID 1413739 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-4cffe51eb4074052abe43f9f4feb9cba
Source dataset
uspto-grants-1981_02
Patent number
US04251454

Reaction notes

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