2-Nitrobenzyl chloride → Diethyl (formylamino)((2-nitrophenyl)methyl)propanedioate

HRID 1648304

Reaktionsgleichung

Reaktionsgleichung von HRID 1648304
[CH:1]([NH:3][CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:2].[N+:15]([C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Cl)([O-:17])=[O:16]>[O-]CC.[Na+]>[CH:1]([NH:3][C:4]([CH2:20][C:19]1[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=1[N+:15]([O-:17])=[O:16])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:2]

Komponenten

4

Edukt 2

HCID 119212-Nitrobenzyl chlorideHCID 80617Diethyl formamidomalonate

Produkt 1

HCID 53819953Diethyl (formylamino)((2-nitrophenyl)methyl)propanedioateAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2723922Sodium ethoxideLösungsmittel

Versuchsvorschrift

Diethyl (formylamino)malonate (20.3 g, 0.1 mol) was added to a stirred solution of sodium ethoxide (250 mL of 0.4 M). 2-Nitrobenzyl chloride (17.2 g, 0.1 mol) was added, the mixture was refluxed for 2 hours and the solvent was then removed under reduced pressure. The material was partitioned between ethyl acetate and water, the ethyl acetate was separated and evaporated to give 40.3 g of crude product. The compound was crystallized from ethyl acetate:hexane to give 25.5 g of diethyl (formylamino)((2-nitrophenyl)methyl)propanedioate; mp 129°-132° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 2 hours
  2. customthe solvent was then removed under reduced pressure
  3. customThe material was partitioned between ethyl acetate and water
  4. customthe ethyl acetate was separated
  5. customevaporated
  6. customto give 40.3 g of crude product
  7. customThe compound was crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-11cce98a32824fc780482f4b13fc88d1
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05436240

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