3-Anilinopropionitrile → HCID 70418397, compound

HRID 542959Notes

Reaction equation

HRID 542959 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.[CH2:15]([O:18][C:19]1[CH:28]=[C:27]([CH:29](O)CS(C)(=O)=O)[CH:26]=[C:25]([O:36][CH2:37][CH:38]=[CH2:39])[C:20]=1[NH:21][C:22](=[O:24])[CH3:23])[CH:16]=[CH2:17]>CS(C)=O>[CH2:15]([O:18][C:19]1[CH:28]=[C:27]([CH2:29][C:12]([C:13]#[N:14])=[CH:11][NH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:26]=[C:25]([O:36][CH2:37][CH:38]=[CH2:39])[C:20]=1[NH:21][C:22](=[O:24])[CH3:23])[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 21280981HCID 21280981, compound

Product 1

HCID 70418397HCID 70418397, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1.4 g. of sodium methylate, 3.75 g. of β-anilino-propionitrile and 6.3 g. of 2',6'-bis(allyloxy)-4'-[1-hydroxy-2-(methylsulfonyl)-ethyl]-acetanilide in 43 ml. of absolute dimethylsulfoxide was stirred at room temperature under an atmosphere of nitrogen and the exclusion of moisture for 3 hours, poured into 200 ml. of water and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried and evaporated. After chromatography on aluminum oxide and recrystallization from ethanol, there was obtained 2',6'-bis-(allyloxy)-4'-(3-anilino-2-cyano-allyl)-acetanilide having a melting point of 176°-178° C.

Workup

  1. additionA mixture of 1.4 g
  2. additionpoured into 200 ml
  3. extractionof water and extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water
  6. customdried
  7. customevaporated
  8. customAfter chromatography on aluminum oxide and recrystallization from ethanol

Sources & evidence

ORD record
ord-ed7cef26895f4044ba161d9a3e59f02f
Source dataset
uspto-grants-1987_04
Patent number
US04659818

Reaction notes

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