Guanidine → Diaveridine

HRID 1855810Notes

Reaction equation

HRID 1855810 reaction equation
C([C:6]([CH:20](OCC)OCC)([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=1)[C:7]#[N:8])(OCC)=O.[OH-].[K+].[NH2:29][C:30]([NH2:32])=[NH:31]>C(O)C>[NH2:32][C:30]1[N:31]=[C:7]([NH2:8])[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)=[CH:20][N:29]=1

Participants

5

Reactant 3

HCID 3520GuanidineHCID 14797Potassium HydroxideHCID 12559142alpha-Carbethoxy-alpha-diethoxymethyl-beta-(3,4-dimethoxyphenyl)propionitrile

Product 1

HCID 21453DiaveridineYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of α-carbethoxy-α-diethoxymethyl-β-(3,4-dimethoxyphenyl)propionitrile (3.75 g) and an equivalent amount of potassium hydroxide in ethanol (70 ml) was heated at reflux for one hour. A solution of guanidine (0.035 mol) in ethanol (50 ml) was added and reflux was resumed. Ethanol was boiled off until the reaction temperature reached 85° C. After 17 hours at reflux the mixture was allowed to cool and the product was filtered and washed with ethanol giving a white solid which was purified as described in Example 5 to yield 1.4 g (54%) of the title compound, m.p. 231°-233° C.

Workup

  1. temperatureat reflux for one hour
  2. temperaturereflux
  3. customreached 85° C
  4. temperatureAfter 17 hours at reflux the mixture
  5. temperatureto cool
  6. filtrationthe product was filtered
  7. washwashed with ethanol giving a white solid which
  8. customwas purified

Sources & evidence

ORD record
ord-2a5fe6a68bd643afa9c6f2fcd5293478
Source dataset
uspto-grants-1980_08
Patent number
US04216319

Reaction notes

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