3-Anilinopropionitrile → HCID 70571269, compound

HRID 441306Notes

Reaction equation

HRID 441306 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-c2b76ae1caab438c8ef5774b3574d4e3
Source dataset
uspto-grants-1977_08
Patent number
US04039543

Reaction notes

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