HCID 23498110, compound → HCID 2304284, compound

HRID 1184207Notes

Reaction equation

HRID 1184207 reaction equation
C([CH:3](CC)[C:4]([CH3:9])([CH3:8])[C:5](=[NH:7])[NH2:6])C.[CH2:12]([O:14][CH:15]=[C:16]([C:20]([O-])=O)[C:17]([O-])=[O:18])[CH3:13].[O-:23]CC.[Na+].C(O)C>C(O)C>[C:4]([C:5]1[NH:6][C:17](=[O:18])[C:16]([C:15]([O:14][CH2:12][CH3:13])=[O:23])=[CH:20][N:7]=1)([CH3:3])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 23498110HCID 23498110, compoundHCID 23706232Ethanol sodium ethoxideHCID 86642212HCID 86642212, compound

Product 1

HCID 2304284HCID 2304284, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of diethyl 2,2-dimethylpropanimidamide m hydrochloride (1.36 g) and (ethoxymethylene)malonate (2.16 g) in ethanol (100 ml) was added 20% sodium ethoxide-ethanol solution (6.8 g) under ice-cooling, and the mixture was stirred at 80° C. for 5 hr. The reaction mixture was concentrated under reduced pressure, 1M hydrochloric acid (10 ml) was added under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, hexane was added to the residue, and the precipitate was collected by filtration to give the object product(1.65 g) as a powder.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, 1M hydrochloric acid (10 ml)
  3. additionwas added under ice-
  4. temperaturecooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. concentrationThe extract was concentrated under reduced pressure, hexane
  7. additionwas added to the residue
  8. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-f194a28fec2644ea8bc22aed9e648682
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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