Benzamidine, hydrochloride → HCID 2765485, compound

HRID 842054Notes

Reaction equation

HRID 842054 reaction equation
[O-]CC.[Na+].Cl.[C:6]([NH2:14])(=[NH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:15](=[C:22]([C:28]([O-])=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[O:29]=[C:28]1[CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:14]=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:13]1

Participants

5

Reactant 3

HCID 80289Benzamidine, hydrochlorideHCID 2723922Sodium ethoxideHCID 713566902-(Ethoxycarbonyl)-3-phenylprop-2-enoate

Product 1

HCID 2765485HCID 2765485, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of a 20% solution of sodium ethoxide in ethanol (44.9 g) and ethanol (200 ml) is added benzamidine hydrochloride (10.3 g) at room temperature. The mixture is stirred at the same temperature for two hours, and thereto is added ethyl benzalmalonate (14.0 g), and the mixture is refluxed for three hours. The reaction mixture is concentrated under reduced pressure, and to the residue is added ice-water. To the mixture is added dropwise conc. hydrochloric acid until the pH value of the mixture is adjusted to pH 4. The precipitates are collected by filtration, and washed with water to give crude ethyl 3,4,5,6-tetrahydro-4-oxo-2,6-diphenylpyrimidine-5-carboxylate (15.8 g).

Workup

  1. temperaturethe mixture is refluxed for three hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additionto the residue is added ice-water
  4. additionTo the mixture is added dropwise conc. hydrochloric acid until the pH value of the mixture
  5. filtrationThe precipitates are collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-b206f5f8925e4191bd50caf7718610bd
Source dataset
uspto-grants-2002_04
Patent number
US06372740B1

Reaction notes

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