N-cyclopropylurea → HCID 86704350, Verbindung

HRID 1507620

Reaktionsgleichung

Reaktionsgleichung von HRID 1507620
[CH:1]1([NH:4][C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.Cl.[NH2:9][C:10](OCC)=[CH:11][C:12](OCC)=[O:13].CC[O-].[Na+]>C(O)C>[NH2:9][C:10]1[NH:7][C:5](=[O:6])[N:4]([CH:1]2[CH2:3][CH2:2]2)[C:12](=[O:13])[CH:11]=1

Komponenten

5

Edukt 3

HCID 272626N-cyclopropylureaHCID 2723922Sodium ethoxideHCID 53395434Ethyl beta-amino-beta-ethoxyacrylate hydrochloride

Produkt 1

HCID 86704350HCID 86704350, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of cyclopropyl urea (10 g, 100 mmol, 1 eq) and ethyl 3-amino-3-ethoxy-acrylate HCl (19.55 g, 100 mmol, 1 eq) in Ethanol (125 ml) was heated at 75° C. for 2 hours. To this solution was added 2 equivalents of NaOEt then heated for an additional one hour. Solvent was evaporated, water (50 ml) was added then acidified via concentrated HCl to pH of 4-5. The resulting precipitate was obtained by filtration and washed with cold water to give the desired product (9.35 g, 56%) after vacuum dried overnight at 40° C.: The desired isomer was determined via 2D-NMR; 1H NMR (400 MHz, DMSO-d6) δ 10.18 (1H), 6.10 (2H), 4.44 (1H), 2.38 (1H), 0.85 (2H), 0.62 (2H); m/z (ES+) 168.17

Aufarbeitung

  1. temperaturethen heated for an additional one hour
  2. customSolvent was evaporated
  3. additionwater (50 ml) was added
  4. customThe resulting precipitate was obtained by filtration
  5. washwashed with cold water

Quellen und Nachweise

ORD-Eintrag
ord-a26f25c2d3b0437ca122b67ffff123c9
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221821B2

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