Diethyl Malonate → HCID 178526553, compound

HRID 75446Notes

Reaction equation

HRID 75446 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](=[NH:10])[NH2:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C[O-].[Na+].[C:16](OCC)(=[O:23])[CH2:17][C:18](OCC)=[O:19]>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]2[N:9]=[C:18]([OH:19])[CH:17]=[C:16]([OH:23])[N:10]=2)=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 1174754-NitrobenzamidineHCID 10942334Sodium Methoxide

Product 1

HCID 178526553HCID 178526553, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 50 mL round-bottomed flask was placed 4-nitrobenzimidamide (55, 0.435 g, 2.63 mmol) in MeOH (4 mL) to give a yellow suspension. Sodium methanolate (25% by wt in MeOH) (1.867 mL, 8.17 mmol) was added. The mixture was stirred at room temperature for 30 min. Diethyl malonate (0.480 mL, 3.16 mmol) was added in drops and stirring was continued at room temperature over 6 days, resulting in an orange suspension. The mixture was concentrated, dissolved in hot water and filtered. The filtrate was made acidic with AcOH to pH3. The resulting light yellow solids were collected by filtration and dried under vacuum to give the title compound (499 mg, 81%) as a light yellow solid. HRMS: For [M+H]+ mass error=−0.0 mDa or −0.17 ppm.

Workup

  1. customIn a 50 mL round-bottomed flask was placed
  2. stirringstirring
  3. waitwas continued at room temperature over 6 days
  4. customresulting in an orange suspension
  5. concentrationThe mixture was concentrated
  6. dissolutiondissolved in hot water
  7. filtrationfiltered
  8. filtrationThe resulting light yellow solids were collected by filtration
  9. customdried under vacuum

Sources & evidence

ORD record
ord-34ea74092a464bd39b298f2557d27d62
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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