4-Amidinobenzamide Hydrochloride → 4-[5-(4-Pentylphenyl)pyrimidin-2-yl]benzamide

HRID 461303Notes

Reaction equation

HRID 461303 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12](=[CH:15]OCC)[CH:13]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].Cl.[C:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH2:29])=[O:28])=[CH:25][CH:24]=1)(=[NH:22])[NH2:21].C[O-].[Na+]>CO>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[N:21][C:20]([C:23]3[CH:31]=[CH:30][C:26]([C:27]([NH2:29])=[O:28])=[CH:25][CH:24]=3)=[N:22][CH:15]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 27242934-Amidinobenzamide HydrochlorideHCID 10942334Sodium MethoxideHCID 53726582HCID 53726582, compound

Product 1

HCID 155640744-[5-(4-Pentylphenyl)pyrimidin-2-yl]benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.46 g. of 2-(4-n-pentylphenyl)-3-ethoxy-acrolein, 3.63 g. of the 4-amidinobenzoic acid amide hydrochloride described above and 0.0254 mol of sodium methylate (obtained by dissolving 0.584 g. of sodium metal in methanol) are suspended in 250 ml. of methanol and stirred overnight at room temperature under an atmosphere of nitrogen. The yellow suspension is then filtered and the residue is washed with a little ethanol and suspended in 1.4 liters of ether for further purification. The suspension is washed with water and then filtered again. Sparingly soluble 4-[5-(4-n-pentylphenyl)-2-pyrimidinyl]benzoic acid amide is obtained.

Workup

  1. filtrationThe yellow suspension is then filtered
  2. washthe residue is washed with a little ethanol
  3. customsuspended in 1.4 liters of ether for further purification
  4. washThe suspension is washed with water
  5. filtrationfiltered again

Sources & evidence

ORD record
ord-66660c8da13f48a6b47a87a9277eecef
Source dataset
uspto-grants-1977_12
Patent number
US04062798

Reaction notes

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