Carbamimidic acid, methyl ester, sulfate (1:1) → HCID 178498443, Verbindung

HRID 1452654Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1452654
[C:1](/[C:4](=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)/[C:5]([O:7][CH3:8])=[O:6])(=O)[CH3:2].S(O)(O)(=O)=O.[CH3:22][O:23][C:24](=[NH:26])[NH2:25].C([O-])(O)=O.[Na+]>C(O)C>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[NH:26][C:24]([O:23][CH3:22])=[N:25][C:1]([CH3:2])=[C:4]2[C:5]([O:7][CH3:8])=[O:6])=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 516892Sodium BicarbonateHCID 10751489methyl (2Z)-2-acetyl-3-(4-fluorophenyl)-2-propenoate

Produkt 1

HCID 178498443HCID 178498443, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of methyl (2Z)-2-acetyl-3-(4-fluorophenyl)-2-propenoate (0.220 mole, 48.8 g), O-methyl isourea hydrogensulfate (53.40 g, 0.310 mol, 1.5 eq.), NaHCO3 (61.74 g, 0.74 mole, 3.5 equiv.) and ethanol (1.2 L) was refluxed for 24 h, cooled to room temperature, and filtered. The solid was washed with ethanol (200 mL) and the combined filtrate was concentrated in vacuo. The residue was purified by chromatography (silica gel, hexanes/EtOAc/Et3N 50:50:0.1) to yield a mixture of tautomers (4:1, 33.0 g, 53.9%). 1H NMR (CDCl3) δ 7.32-7.24 (m, 2H), 7.04-6.95 (m, 2H), 5.81 (s, 1H), 5.38 (d, 1H, J=2.9 Hz), 4.00 (s, 3H), 3.63 (s, 3H), 2.34 (s, 3H).

Aufarbeitung

  1. temperaturewas refluxed for 24 h
  2. filtrationfiltered
  3. washThe solid was washed with ethanol (200 mL)
  4. concentrationthe combined filtrate was concentrated in vacuo
  5. customThe residue was purified by chromatography (silica gel, hexanes/EtOAc/Et3N 50:50:0.1)
  6. customto yield
  7. additiona mixture of tautomers (4:1, 33.0 g, 53.9%)

Quellen und Nachweise

ORD-Eintrag
ord-960bda8449c34f0fade8e1af02e30c9b
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473698B2

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