Water → 3-Oximino-5-dichloromethyl-2-phthalimidopyrazine

HRID 4442

Reaktionsgleichung

Reaktionsgleichung von HRID 4442
C([C:3]1[C:4]([N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])=[N:5][CH:6]=[C:7]([CH:9]([Cl:11])[Cl:10])[N:8]=1)=O.Cl.[NH2:24][OH:25].O>CS(C)=O>[N:24](=[C:3]1[N:8]=[C:7]([CH:9]([Cl:11])[Cl:10])[CH:6]=[N:5][CH:4]1[N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])[OH:25]

Komponenten

5

Edukt 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 136047783-Formyl-5-dichloromethyl-2-phthalimidopyrazine

Produkt 1

HCID 1363937243-Oximino-5-dichloromethyl-2-phthalimidopyrazineAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A solution of 10 g of 3-formyl-5-dichloromethyl-2-phthalimidopyrazine in 50 ml of dimethyl sulfoxide was heated at 50° C., 7 g of hydroxylamine hydrochloride were added, and the mixture was stirred for 15 minutes at 70° C. Thereafter, 700 ml of water were added to the reaction solution, the mixture was filtered and the filtrate was washed with a little diethyl ether. 6.8 g of colorless crystals (65%) of 3-oximinodichloromethyl-2-phthalimidopyrazine were obtained. 1H-NMR (270 MHz, DMSO-d6): δ7.7 (s, 1H), 8.0 (m, 4H), 8.3 (s, 1HO), 9.1 (s, 1H), 12.0 (s, OH).

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. washthe filtrate was washed with a little diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e962f65fda1a436697d07c873020f372
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725689

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