Sulfuric Acid → 3-Anilinoprop-2-enenitrile

HRID 2058799Notes

Reaction equation

HRID 2058799 reaction equation
S(=O)(=O)(O)O.[Na].O[CH:8]=[CH:9][C:10]#[N:11].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[NH:12]([CH:8]=[CH:9][C:10]#[N:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6115AnilineHCID 86738287Sodium 3-hydroxyacrylonitrile

Product 1

HCID 692608743-Anilinoprop-2-enenitrileYield 67.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

12.25 g (0.125 mol) of sulfuric acid in 30 ml of ethanol is added drop by drop, at 0° C., to a suspension of 32.5 g (0.25 mol) of sodium-3-hydroxyacrylonitrile and 32.6 g (0.35 mol) of aniline in 150 ml of ethanol, and the mixture is held at 25° C. for 5 h. After removal of the solid by filtration and withdrawal of the solvent, the product is dissolved with water, acidified with dilute sulfuric acid, and extracted with ether. After recrystallization of the concentrated ether extract from carbon tetrachloride, 24.3 g (67.6%) of 3-anilinoacrylonitrile is obtained.

Workup

  1. customAfter removal of the solid
  2. filtrationby filtration and withdrawal of the solvent
  3. dissolutionthe product is dissolved with water
  4. extractionextracted with ether
  5. customAfter recrystallization of the concentrated ether
  6. extractionextract from carbon tetrachloride

Sources & evidence

ORD record
ord-a680c47d249247bc8b32a323b624c837
Source dataset
uspto-grants-1982_03
Patent number
US04319024

Reaction notes

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