Guanidine → Ormetoprim

HRID 614285Notes

Reaction equation

HRID 614285 reaction equation
C([C:6]([CH:21](OCC)OCC)([CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:11]=1[CH3:20])[C:7]#[N:8])(OCC)=O.[OH-].[K+].[NH2:30][C:31]([NH2:33])=[NH:32]>C(O)C>[NH2:33][C:31]1[N:32]=[C:7]([NH2:8])[C:6]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:11]=2[CH3:20])=[CH:21][N:30]=1

Participants

5

Reactant 3

HCID 3520GuanidineHCID 14797Potassium HydroxideHCID 12559127HCID 12559127, compound

Product 1

HCID 23418Ormetoprim

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of α-carbethoxy-α-diethoxymethyl-β-(4,5-dimethoxy-2-methylphenyl)propionitrile (3.9 g, 0.01 mol) 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 20 hours at reflux the mixture was allowed to cool, and the product was filtered and washed with ethanol giving 2.57 g (94%) of nearly white solid. After purification as described in Example 5, the product was dried under reduced pressure giving a white solid, m.p. 231°-233° C.

Workup

  1. temperatureat reflux for one hour
  2. temperaturereflux
  3. customreached 85° C
  4. temperatureAfter 20 hours at reflux the mixture
  5. temperatureto cool
  6. filtrationthe product was filtered
  7. washwashed with ethanol giving 2.57 g (94%) of nearly white solid
  8. customAfter purification
  9. customthe product was dried under reduced pressure
  10. customgiving a white solid, m.p. 231°-233° C.

Sources & evidence

ORD record
ord-bfbea14066cc486ab05c9426d8e411ef
Source dataset
uspto-grants-1979_03
Patent number
US04144263

Reaction notes

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