3-Anilinopropionitrile → HCID 70569613, compound

HRID 1413732Notes

Reaction equation

HRID 1413732 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]1[C:4]([O:21][CH3:22])=[C:5]([CH:11]=[C:12]([CH:14](O)CS(C)(=O)=O)[CH:13]=1)[N:6]([CH3:10])[C:7](=[O:9])[CH3:8].C[O-].[Na+].[NH:27]([CH2:34][CH2:35][C:36]#[N:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CS(C)=O>[NH:27]([CH:34]=[C:35]([C:36]#[N:37])[CH2:14][C:12]1[CH:13]=[C:3]([N:2]([CH3:23])[CH3:1])[C:4]([O:21][CH3:22])=[C:5]([CH:11]=1)[N:6]([CH3:10])[C:7](=[O:9])[CH3:8])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 20290381HCID 20290381, compound

Product 1

HCID 70569613HCID 70569613, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 10.6 g. of 3'-dimethylamino-5'-[1-hydroxy-2-(methylsulfonyl)-ethyl]-2'-methoxy-N-methylacetanilide, 1.8 g. of sodium methylate and 4.8 g. of β-anilinopropionitrile in 20 ml. of dimethylsulfoxide was stirred with the exclusion of moisture for 5 hours at 50° C. The mixture was poured into 250 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 benzene and recrystallization from ethyl acetate/petroleum ether, there was obtained the 5'-(3-anilino-2-cyanoallyl)-3'-dimethylamino-2'-methoxy-N-methylacetanilide, having a melting point of 176°-178° C.

Workup

  1. additionA mixture of 10.6 g
  2. additionThe mixture was poured into 250 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 benzene and recrystallization from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-4a3b4363ba17411b8d173645ae6771a0
Source dataset
uspto-grants-1981_02
Patent number
US04251454

Reaction notes

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