Diethyl 2-(ethoxymethylidene)-3-oxobutanedioate → HCID 19958265, compound

HRID 1449457Notes

Reaction equation

HRID 1449457 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([CH3:7])[CH:3]=1.C(O[CH:11]=[C:12]([C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])C>C(O)(=O)C>[CH3:7][C:4]1[C:3]2[C:2](=[N:1][C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:11]=2)[O:6][N:5]=1

Participants

4

Reactant 2

HCID 40590Diethyl 2-(ethoxymethylidene)-3-oxobutanedioateHCID 845905-Amino-3-methylisoxazole

Product 1

HCID 19958265HCID 19958265, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Amino-3-methylisoxazole (12.25 g, 0.125 mol) and diethyl (ethoxymethylene)oxalacetate (33.55 g, 0.138 mol) are dissolved in 200 mL glacial acetic acid under an N2 atmosphere. The solution is heated to reflux for two hours, then stirred at room temperature for 65 hours. The solution is poured into ice water, causing the precipitation of a red solid. The solid is collected by filtration, redissolved in 175 mL glacial acetic acid and reprecipitated with the addition of ice. The resulting yellow solid is collected by filtration and air dried, giving 14.20 g of product, yield 40.8%, having melting point 95°-99° C. A small amount is recrystallized from hexanes/ethyl acetate, melting point 100°-101° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for two hours
  3. customthe precipitation of a red solid
  4. filtrationThe solid is collected by filtration
  5. dissolutionredissolved in 175 mL glacial acetic acid
  6. customreprecipitated with the addition of ice
  7. filtrationThe resulting yellow solid is collected by filtration and air
  8. customdried

Sources & evidence

ORD record
ord-35215b97b0ee46bba08ebc465657bc8e
Source dataset
uspto-grants-1997_02
Patent number
US05599772

Reaction notes

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