Acetic Acid → 4,6-Dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde oxime

HRID 1454463Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1454463
Cl.[NH2:2][OH:3].CC(O)=O.[Cl:8][C:9]1[C:14]([CH:15]=O)=[C:13]([Cl:17])[N:12]=[C:11]([S:18][CH3:19])[N:10]=1>CCO>[Cl:8][C:9]1[C:14]([CH:15]=[N:2][OH:3])=[C:13]([Cl:17])[N:12]=[C:11]([S:18][CH3:19])[N:10]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 443297Hydroxyamine hydrochlorideHCID 46140044,6-Dichloro-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

Produkt 1

HCID 218222514,6-Dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde oximeAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To the mixture of hydroxylamine hydrochloride (139 mg, 2.0 mmol), HOAc (0.113 mL, 2.0 mmol) and EtOH (5 mL) was added 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde (223 mg, 1.0 mol) to room temperature. The solution was then heated at 50° C. for about 1 hour, 60° C. for about 30 minutes and 70° C. for about 30 minutes before it was concentrated under vacuum and washed with H2O (10-20 mL) to afford 4,6-dichloro-2-(methylthio)-5-pyrimidinecarbaldehyde oxime (190 mg, 80%). LC-MS m/z 238 (M+H)+1.57 minute, 1.65 minute; 1H-NMR (CDCl3) δ 2.62, 2.65 (3 H), 7.53, 8.30 (1 H).

Aufarbeitung

  1. concentrationwas concentrated under vacuum
  2. washwashed with H2O (10-20 mL)

Quellen und Nachweise

ORD-Eintrag
ord-ca86484bf2ab4fff8bc65231714104a0
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07479558B2

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