3-Anilinopropionitrile → HCID 70570823, compound

HRID 441320Notes

Reaction equation

HRID 441320 reaction equation
[Cl:1][C:2]1[C:14]([NH:15][CH3:16])=[CH:13][C:5]([CH:6](O)CS(C)(=O)=O)=[CH:4][C:3]=1[NH:17][CH3:18].C[O-].[Na+].[NH:22]([CH2:29][CH2:30][C:31]#[N:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CS(C)=O>[NH:22]([CH:29]=[C:30]([CH2:6][C:5]1[CH:13]=[C:14]([NH:15][CH3:16])[C:2]([Cl:1])=[C:3]([NH:17][CH3:18])[CH:4]=1)[C:31]#[N:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 53867801HCID 53867801, compound

Product 1

HCID 70570823HCID 70570823, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 13.2 g. of 4-chloro-3,5-bis(methylamino)-α-[(methylsulfonyl)-methyl]benzyl alcohol, 3.6 g. of sodium methylate and 9.6 g. of β-anilinopropionitrile in 80 ml. of dimethylsulfoxide was stirred for 5 hours under nitrogen at 50° C. 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. By purification of the residue over aluminum oxide with benzene and recrystallization from ethyl acetate/petroleum ether, there was obtained α-(anilinomethylene)-4-chloro-3,5-bis(methylamino)hydrocinnamonitrile having a melting point of 142°-147° C.

Workup

  1. additionA mixture of 13.2 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. customBy purification of the residue over aluminum oxide
  7. customwith benzene and recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-31393678ea964b50a6f4a3e07e0238f4
Source dataset
uspto-grants-1977_08
Patent number
US04039543

Reaction notes

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