Chloroacetic Acid → 2-(2-Oxo-1,2-dihydropyrimidin-1-yl)acetic acid

HRID 887105

Reaktionsgleichung

Reaktionsgleichung von HRID 887105
Cl.[OH:2][C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1.Cl[CH2:10][C:11]([OH:13])=[O:12].[OH-].[Na+].Cl>>[O:2]=[C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]1[CH2:10][C:11]([OH:13])=[O:12]

Komponenten

5

Edukt 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178479648HCID 178479648, Verbindung

Produkt 1

HCID 10964092-(2-Oxo-1,2-dihydropyrimidin-1-yl)acetic acid

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To 2-hydroxypyrimidine hydrochloride (1.00 g, 7.54 mmol) and chloroacetic acid (0.713 g, 7.54 mmol) was added 5 N sodium hydroxide solution (4.5 mL). The reaction mixture was heated at 105° C. for 2 h. After cooled down to ambient temperature and neutralized with 2 M hydrochloric acid (3.8 mL), the title compound was collected by crystallization and filtration as a pale yellow solid. 1H NMR (DMSO-d6): δ 13.2 (s, 1H), 8.59 (dd, J=3.9, 3.0 Hz, 1H), 8.16 (dd, J=6.4, 2.8 Hz, 1H), 6.46 (dd, J=6.4, 4.1 Hz, 1H), 4.58 (s, 2H). LC/MS 155.2 (M+1).

Aufarbeitung

  1. filtrationthe title compound was collected by crystallization and filtration as a pale yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-7630fb6804ef43c2b6d0b67b06d73dd0
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247415B2

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