Dimethylformamide → HCID 54137088, compound

HRID 237141Notes

Reaction equation

HRID 237141 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]\[C:4]([O-:6])=[O:5].[Na+].[C:11]1([CH2:17][C:18]#[N:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CN(C)C=O>>[C:18]([CH:17]([CH:2]([CH2:3][C:4]([OH:6])=[O:5])[C:1]([O:8][CH3:9])=[O:7])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)#[N:19]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8794PhenylacetonitrileHCID 23681663Sodium methyl maleate

Product 1

HCID 54137088HCID 54137088, compoundYield 87.9%

Procedure

Into a 200 ml, one-neck flask is placed 35 grams of sodium methyl maleate (0.23 moles), 85 grams (0.73 moles) of phenyl acetonitrile and 80 g(1.1 moles) dimethyl formamide. The reaction mixture is heated to 125°-140° C. for five hours and then distilled in vacuo. The residue is extracted three times with 300 ml ether. The solid (56 grams) is then dissolved in water and acidified with 23 grams conc. HCl in 50 mls water. The liquid that separates out is dissolved in ether and washed with water to remove unreacted starting materials. The ether is distilled off to give a residue of 50 grams of product (yield: 88°). The structure is verified by NMR (in CDCl3): ##STR57## CH2 (a) ABX multiplet at 2.50-3.00δ CH(b) multiplet, 3.30-3.56δ

Workup

  1. temperatureThe reaction mixture is heated to 125°-140° C. for five hours
  2. distillationdistilled in vacuo
  3. extractionThe residue is extracted three times with 300 ml ether
  4. dissolutionThe solid (56 grams) is then dissolved in water
  5. dissolutionThe liquid that separates out is dissolved in ether
  6. washwashed with water
  7. customto remove unreacted
  8. distillationThe ether is distilled off

Sources & evidence

ORD record
ord-97b22b9e41d94afd9c8a3a41ed883d86
Source dataset
uspto-grants-1979_06
Patent number
US04159388

Reaction notes

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