Water → HCID 178518202, compound

HRID 271396

Reaction equation

HRID 271396 reaction equation
[Na].[C:2]1([CH:8]([C:12]([NH2:14])=[O:13])[C:9]([NH2:11])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15](OCC)=O.O>C(O)C>[C:2]1([C:8]2[C:12]([OH:13])=[N:14][CH:15]=[N:11][C:9]=2[OH:10])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8025Ethyl formateHCID 27475362-PhenylmalonamideHCID 5360545Sodium

Product 1

HCID 178518202HCID 178518202, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Sodium metal (0.92 g, 40 mmol) was dissolved by stirring in ethanol (30 mL) at room temperature under argon over 40 min. To the resulting solution at room temperature was added 2-phenylmalonamide (3.56 g, 20 mmol) and ethyl formate (1.9 mL, 24 mmol). The resulting suspension was heated at 50° C. under argon 16 h. After cooling the reaction mixture to room temperature, water (100 mL) was added and the mixture was stirred for 1 h. Solid was removed by filtration. The filtrate was acidified to pH˜4 with 1 M aqueous HCl. The resulting precipitate was collected by filtration and further washed with water (20 mL×2), then Et2O (10 mL×2). After drying under vacuum for 3 h, the title compound (2.6 g) was obtained as a light yellow solid. HPLC/MS: retention time=0.76 min, [M+H]+=189.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. customSolid was removed by filtration
  3. filtrationThe resulting precipitate was collected by filtration
  4. washfurther washed with water (20 mL×2)
  5. customAfter drying under vacuum for 3 h

Sources & evidence

ORD record
ord-688288197ef7443e83e0b009843faba2
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Linked notes

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