Ethyl 2-methylacetoacetate → HCID 135527547, compound

HRID 1740843Notes

Reaction equation

HRID 1740843 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.[CH3:15][CH:16]([C:22]([CH3:24])=O)[C:17](OCC)=[O:18]>C(O)C>[CH3:15][C:16]1[C:17](=[O:18])[NH:13][C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:14][C:22]=1[CH3:24]

Participants

5

Reactant 3

HCID 701Ethyl 2-methylacetoacetateHCID 80289Benzamidine, hydrochlorideHCID 2723922Sodium ethoxide

Product 1

HCID 135527547HCID 135527547, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of sodium ethoxide (31.3 g) and anhydrous ethanol (200 ml) is added benzamidine hydrochloride (23.9 g) at 0-5° C. The mixture is stirred at 0° C. for 30 minutes, and thereto is added dropwise a solution of ethyl 2-methylacetoacetate (20 g) and anhydrous ethanol (50 ml) at the same temperature. After addition, the mixture is stirred at room temperature for 30 minutes, and refluxed for six hours. The reaction mixture is concentrated under reduced pressure, and the residue is dissolved in water. The pH value of the mixture is adjusted to pH 4 by addition of conc. hydrochloric acid while the mixture is stirred at 0-5° C. The precipitates are collected by filtration, washed with water, further washed with diethyl ether, and recrystallized from ethanol to give the desired compound (14.3 g), m.p. 205-207° C.

Workup

  1. additionAfter addition
  2. stirringthe mixture is stirred at room temperature for 30 minutes
  3. temperaturerefluxed for six hours
  4. concentrationThe reaction mixture is concentrated under reduced pressure
  5. dissolutionthe residue is dissolved in water
  6. additionThe pH value of the mixture is adjusted to pH 4 by addition of conc. hydrochloric acid while the mixture
  7. stirringis stirred at 0-5° C
  8. filtrationThe precipitates are collected by filtration
  9. washwashed with water
  10. washfurther washed with diethyl ether
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-40c172914f854a6ab57254a839d9f85a
Source dataset
uspto-grants-1999_10
Patent number
US05972946

Reaction notes

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