Acetamidomalonic acid diethyl ester → Diethyl acetamido[5-(4-nitrophenyl)furfuryl]malonate

HRID 1833418

Reaction equation

HRID 1833418 reaction equation
[Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)([O-:19])=[O:18]>C(O)C>[C:2]([NH:5][C:6]([CH2:30][C:29]1[O:32][C:26]([C:23]2[CH:24]=[CH:25][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=2)=[CH:27][CH:28]=1)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 14041Acetamidomalonic acid diethyl esterHCID 5360545SodiumHCID 152120842-(Chloromethyl)-5-(4-nitrophenyl)furan

Product 1

HCID 53706585Diethyl acetamido[5-(4-nitrophenyl)furfuryl]malonateYield 50.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 300 ml of absolute ethanol was added in portions 2.4 g (0.104 mole) of sodium followed by 21.7 g (0.10 mole) of diethyl acetamidomalonate and stirring was continued for 10 minutes. 5-(4-Nitrophenyl)furfuryl chloride (23.7 g, 0.10 mole) was then added in portions, and the mixture was heated under reflux for 5 hrs. The mixture was filtered hot to remove the insoluble sodium chloride. The filtrate was cooled in a refrigerator, and the solid which was deposited was collected by filtration and washed with ether. The solid was stirred in water, collected by filtration, and dried in an oven at 100° for 2 hrs. to give 21 g (50%) of diethyl acetamido[5-(4-nitrophenyl)furfuryl]malonate. Recrystallization from SDA-32 gave an analytical sample, m.p. 183°-185°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. filtrationThe mixture was filtered hot
  4. customto remove the insoluble sodium chloride
  5. temperatureThe filtrate was cooled in a refrigerator
  6. filtrationthe solid which was deposited was collected by filtration
  7. washwashed with ether
  8. stirringThe solid was stirred in water
  9. filtrationcollected by filtration
  10. customdried in an oven at 100° for 2 hrs

Sources & evidence

ORD record
ord-c86a387e19df4205a3d015e04f3fad65
Source dataset
uspto-grants-1978_01
Patent number
US04066669

Linked notes

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