Dimethyl Sulfoxide → HCID 70569108, compound

HRID 1413745Notes

Reaction equation

HRID 1413745 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:23]=[C:24]([NH:34][CH3:35])[C:25]([CH3:33])=[C:26]([CH:32]=1)[N:27]([CH3:31])[C:28](=[O:30])[CH3:29])CS(C)(=O)=O.CS(C)=O>O>[NH:4]([CH:11]=[C:12]([C:13]#[N:14])[CH2:16][C:22]1[CH:23]=[C:24]([NH:34][CH3:35])[C:25]([CH3:33])=[C:26]([CH:32]=1)[N:27]([CH3:31])[C:28](=[O:30])[CH3:29])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 141003-AnilinopropionitrileHCID 10942334Sodium MethoxideHCID 20290440HCID 20290440, compound

Product 1

HCID 70569108HCID 70569108, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 27 g. of sodium methylate, 41 g. of β-anilinopropionitrile and 79.5 g. of 5'-[1-hydroxy-2-(methylsulfonyl)ethyl]-N,2'-dimethyl-3'-methylaminoacetanilide in 350 ml. of absolute dimethylsulfoxide was stirred for 1 hour at 50°C., then diluted with 2 liters of water and extracted with 6 liters of ethyl acetate. The ethyl acetate extract was washed with 1 liter of water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on 2 kg. of silica gel with ethyl acetate/methylene chloride (1:1), there being obtained 5'-(3-anilino-2-cyanoallyl)-N,2'-dimethyl-3'-methylaminoacetanilide as an oil.

Workup

  1. additionA mixture of 27 g
  2. extractionextracted with 6 liters of ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with 1 liter of water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on 2 kg

Sources & evidence

ORD record
ord-7baec7932fe84fd084cf7597c0a37487
Source dataset
uspto-grants-1981_02
Patent number
US04251454

Reaction notes

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