Hydrochloric Acid → 1,2-Benzenedicarbonitrile, 4-nitro-

HRID 1833873

Reaktionsgleichung

Reaktionsgleichung von HRID 1833873
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([NH2:15])=O)[C:7](=[CH:11][CH:12]=1)[C:8]([NH2:10])=O)([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O.Cl>N1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([C:13]#[N:15])[C:7](=[CH:11][CH:12]=1)[C:8]#[N:10])([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 831671,2-Benzenedicarboxamide, 4-nitro-

Produkt 1

HCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

4-nitrophthalamide (220g; 1.05 moles) is suspended in pyridine (840 ml). Into this vigorously stirred suspension, phosphorus oxychloride (220 ml; 2.40 moles) is added at such a rate that the reaction maintains a temperature range of 65°-70° C during the 30 minute addition time. The same temperature is maintained an additional hour by external heating. The resulting mixture is neutralized with 12 N hydrochloric acid (150 ml). The purple solid is collected by filtration and dried. The residue is extracted with ethyl acetate (3 × 700 ml) and the purple extract is decolorized with activated charcoal, washed first with 0.4 N sodium hydroxide saturated with sodium chloride (3 × 70 ml) and then with water (4 × 70 ml). Drying and evaporation of the extract leaves 91g of II as pale yellow crystals; yield, 50%, mp 142°-144° C; lit. (7) mp 138°-139° C; lit. (4) 142° C.

Aufarbeitung

  1. customa temperature range of 65°-70° C
  2. additionduring the 30 minute addition time
  3. temperatureThe same temperature is maintained an additional hour by external heating
  4. filtrationThe purple solid is collected by filtration
  5. customdried
  6. extractionThe residue is extracted with ethyl acetate (3 × 700 ml)
  7. extractionthe purple extract
  8. washwashed first with 0.4 N sodium hydroxide saturated with sodium chloride (3 × 70 ml)
  9. customDrying
  10. customevaporation of the extract

Quellen und Nachweise

ORD-Eintrag
ord-5e3b26b05df54046a2b8e62aabd68819
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04067860

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