3-Anilinopropionitrile → HCID 70418853, compound

HRID 542938Notes

Reaction equation

HRID 542938 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.O[CH:16]([C:22]1[CH:31]=[C:30]([O:32][CH3:33])[C:25]([NH:26][C:27](=[O:29])[CH3:28])=[C:24]([O:34][CH3:35])[CH:23]=1)CS(C)(=O)=O>CS(C)=O>[NH:4]([CH:11]=[C:12]([C:13]#[N:14])[CH2:16][C:22]1[CH:31]=[C:30]([O:32][CH3:33])[C:25]([NH:26][C:27](=[O:29])[CH3:28])=[C:24]([O:34][CH3:35])[CH:23]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 21280994HCID 21280994, compound

Product 1

HCID 70418853HCID 70418853, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3.78 g. of sodium methylate, 5.1 g. of β-anilino-propionitrile and 9.8 g. of 4'-[(1-hydroxy-2-(methylsulfonyl)-ethyl)]-2',6'-dimethoxy-acetanilide in 40 ml. of dimethylsulfoxide was stirred at 50° C. for 4 hours with the exclusion of moisture. The mixture was poured into 400 ml. of water and the resulting emulsion was extracted with three 500 ml. portions of ethyl acetate. The ethyl acetate extracts were washed with two 200 ml. portions of water, combined, dried over magnesium sulfate and evaporated under vacuum. Recrystallization of the residue from ethyl acetate gave 4'-(3-anilino-2-cyano-allyl)-2',6'-dimethoxy-acetanilide having a melting point of 165°-167° C.

Workup

  1. additionA mixture of 3.78 g
  2. additionThe mixture was poured into 400 ml
  3. extractionof water and the resulting emulsion was extracted with three 500 ml
  4. washThe ethyl acetate extracts were washed with two 200 ml
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under vacuum
  7. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-f670c651ed0b48a68bc318807b74e07f
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

Loading…