3-Anilinopropionitrile → HCID 70571269, compound

HRID 1413737Notes

Reaction equation

HRID 1413737 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:9]=[C:10]([CH:18]=[C:19]([N:22]3[C:26]([CH3:27])=[CH:25][CH:24]=[C:23]3[CH3:28])[C:20]=2[CH3:21])[CH:11](O)CS(C)(=O)=O)[C:4]([CH3:7])=[CH:5][CH:6]=1.C[O-].[Na+].[NH:32]([CH2:39][CH2:40][C:41]#[N:42])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CS(C)=O>[NH:32]([CH:39]=[C:40]([CH2:11][C:10]1[CH:18]=[C:19]([N:22]2[C:23]([CH3:28])=[CH:24][CH:25]=[C:26]2[CH3:27])[C:20]([CH3:21])=[C:8]([N:3]2[C:2]([CH3:1])=[CH:6][CH:5]=[C:4]2[CH3:7])[CH:9]=1)[C:41]#[N:42])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 54333505HCID 54333505, compound

Product 1

HCID 70571269HCID 70571269, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4.95 g. of 3,5-bis(2,5-dimethylpyrrol-1-yl)-4-methyl-α-[(methylsulfonyl)methyl]benzyl alcohol, 0.95 g. of sodium methylate and 2.16 g. of β-anilinopropionitrile in 13 ml. of dimethylsulfoxide was stirred with the exclusion of moisture for 5 hours at 50° C. The mixture was poured into 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 ethyl acetate and recrystallization from ethyl acetate, there was obtained α-(anilinomethylene)-3,5-bis(2,5-dimethylpyrrol-1-yl)-4-methylhydrocinnamonitrile, having a melting point of 252° C.

Workup

  1. additionA mixture of 4.95 g
  2. additionThe mixture was poured into 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 ethyl acetate and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-5c5f72a4b1f0455989f2ddca8c54755b
Source dataset
uspto-grants-1981_02
Patent number
US04251454

Reaction notes

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