3-Anilinopropionitrile → 4'-(3-Anilino-2-cyano-allyl)-2',6'-dimethoxy-formanilide

HRID 414528Notes

Reaction equation

HRID 414528 reaction equation
C[O-].[Na+].[NH:4]([CH2:11][CH2:12][C:13]#[N:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:15][O:16][C:17]1[CH:25]=[C:24]([CH:26]=O)[CH:23]=[C:22]([O:28][CH3:29])[C:18]=1[NH:19][CH:20]=[O:21]>CS(C)=O>[NH:4]([CH:11]=[C:12]([C:13]#[N:14])[CH2:26][C:24]1[CH:23]=[C:22]([O:28][CH3:29])[C:18]([NH:19][CH:20]=[O:21])=[C:17]([O:16][CH3:15])[CH:25]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 212810192',6'-Dimethoxy-4'-formyl-formanilide

Product 1

HCID 867400924'-(3-Anilino-2-cyano-allyl)-2',6'-dimethoxy-formanilide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2.7 g. of sodium methylate, 3.65 g. of β-anilino-propionitrile and 4.2 g. of 2',6'-dimethoxy-4'-formyl-formanilide in 30 ml. of absolute dimethylsulfoxide was stirred at 50° C. for 30 minutes. The solution was poured into 500 ml. of water and the resulting emulsion extracted with two 500 ml. portions of ethyl acetate. The ethyl acetate extract was washed with two 300 ml. portions of water, dried over magnesium sulfate and evaporated under vacuum. The residue was recrystallized from ethyl acetate and there was obtained 4'-(3-anilino-2-cyano-allyl)-2',6'-dimethoxy-formanilide having a melting point of 186°-187° C.

Workup

  1. additionA mixture of 2.7 g
  2. additionThe solution was poured into 500 ml
  3. extractionof water and the resulting emulsion extracted with two 500 ml
  4. extractionThe ethyl acetate extract
  5. washwas washed with two 300 ml
  6. dry with materialportions of water, dried over magnesium sulfate
  7. customevaporated under vacuum
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f1c857f9cea840d6aa9c443d87ce43ad
Source dataset
uspto-grants-1988_12
Patent number
US04792557

Reaction notes

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