Hydrochloric Acid → 5,6-Dichloro-2,3-dicyanopyrazine

HRID 402310

Reaktionsgleichung

Reaktionsgleichung von HRID 402310
O=[C:2]1[C:7](=O)[NH:6][C:5]([C:9]#[N:10])=[C:4]([C:11]#[N:12])[NH:3]1.S(Cl)([Cl:15])=O.[ClH:17]>CN(C)C=O>[Cl:17][C:2]1[C:7]([Cl:15])=[N:6][C:5]([C:9]#[N:10])=[C:4]([C:11]#[N:12])[N:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 5954711,4,5,6-Tetrahydro-5,6-dioxo-2,3-pyrazinedicarbonitrile

Produkt 1

HCID 6078205,6-Dichloro-2,3-dicyanopyrazineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

FIG. 13 shows the reaction pathway. This reaction should be carried out in a fume hood. In a 500 mL round-bottomed flask with a 24/40 ground-glass joint attached to an efficient reflux condenser and under a nitrogen atmosphere, a magnetically stirred slurry consisting of 8.10 g (0.050 mol) of 1,4,5,6-tetrahydro-5,6-dioxo-2,3-pyrazinedicarbonitrile, 4.0 mL of dimethylformamide 306 and 160 mL of thionyl chloride 1301 was heated. Gas evolution began at ca. 62° [SO2 & HCl gasses evolved]. After about 3.5 hours, the solid had dissolved and the temperature had risen to 70°. After cooling to room temperature, a Dry Ice/acetone bath was applied until the temperature of the reaction medium was −65°. The crystals which formed were collected by rapid filtration of the cold slurry through a sintered-glass filter under a nitrogen blanket. The solid was washed twice with 150-ml portions of cold diethyl ether and air-dried to give 7 g (70%) of 2,3-dichloro-5,6-dicyanopyrazine 301, mp 180-182°. Crystallization of the product may be accomplished if dark, from ˜50 mL of chloroform with carbon treatment to give 5.5 g of purified product.

Aufarbeitung

  1. customThis reaction
  2. customIn a 500 mL round-bottomed flask with a 24/40 ground-glass joint attached to an efficient reflux condenser and under a nitrogen atmosphere
  3. temperaturewas heated
  4. custombegan at ca. 62°
  5. dissolutionthe solid had dissolved
  6. customhad risen to 70°
  7. customa Dry Ice/acetone bath was applied until the temperature of the reaction medium
  8. customwas −65°
  9. customThe crystals which formed
  10. filtrationwere collected by rapid filtration of the cold slurry through a sintered-glass
  11. filtrationfilter under a nitrogen blanket
  12. washThe solid was washed twice with 150-ml portions of cold diethyl ether
  13. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-5ec7d56a89d54c3783a6ddb1e0ecc039
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742107B1

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