Vanillin → HCID 281788, compound

HRID 1586634Notes

Reaction equation

HRID 1586634 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[C:12]([CH2:14][C:15]([NH2:17])=[O:16])#[N:13]>N1CCCCC1.Cl.C(O)C>[C:12]([C:14](=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1)[C:15]([NH2:17])=[O:16])#[N:13]

Participants

6

Reactant 2

HCID 1183VanillinHCID 7898Cyanoacetamide

Product 1

HCID 281788HCID 281788, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A reaction mixture of vanillin (1.52 g, 0.01 mol), α-cyanoacetamide (0.84 g, 0.01 mol), ethanol (25 mL) and piperidine (6 drops) is heated at reflux for 1 hour and then allowed to cool to room temperature. The reaction mixture is acidified to pH of about 3-4 by addition of a few drops of concentrated HCl. The product which is collected by filtration, washed with ethanol and dried in air has the following structure supported by mass spectrometry: ##STR23## The yield of product is 1.5 g (68.8%). In methylene chloride the product has an absorption maximum of 352 nm.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe product which is collected by filtration
  4. washwashed with ethanol
  5. customdried in air

Sources & evidence

ORD record
ord-006f8a62d54a4fdca24452d8aa38df94
Source dataset
uspto-grants-1993_06
Patent number
US05215876

Reaction notes

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