Hydrochloric Acid → HCID 20535132, Verbindung

HRID 1156610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1156610
[NH2:1][C:2]1[N:7]2[O:8][C:9](=[O:11])[N:10]=[C:6]2[N:5]=[C:4]([N:12]([CH2:16][CH:17]=[CH2:18])[CH2:13][CH:14]=[CH2:15])[N:3]=1.C(Cl)(Cl)Cl.[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26](Cl)=[O:27].Cl>O.C(N(CC)CC)C>[Cl:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:25]=1[C:26]([NH:1][C:2]1[N:7]2[O:8][C:9](=[O:11])[N:10]=[C:6]2[N:5]=[C:4]([N:12]([CH2:16][CH:17]=[CH2:18])[CH2:13][CH:14]=[CH2:15])[N:3]=1)=[O:27]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 783922,6-Dichlorobenzoyl chlorideHCID 20535125HCID 20535125, Verbindung

Produkt 1

HCID 20535132HCID 20535132, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

5.0 g. of 7-amino-5-diallylamino-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-2-one are mixed with 150 ml. of chloroform, 10 ml. of triethylamine and 4.5 ml. of 2,6-dichlorobenzoyl chloride and heated to reflux for 7 hours. The mixture is then cooled, diluted with water, adjusted to pH 4 with hydrochloric acid and extracted with chloroform. The combined organic extracts are dried over sodium sulfate and evaporated to dryness under reduced pressure. The residue is chromatographed over silica gel using a mixture of methylene chloride and methanol (99:1) for the elution. Recrystallization from diisopropyl ether and methylene chloride yields pure 2,6-dichloro-N-{5-diallylamino-2-oxo-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-7-yl}benzamide having a melting point of 133°-135° C.

Aufarbeitung

  1. temperatureto reflux for 7 hours
  2. temperatureThe mixture is then cooled
  3. extractionextracted with chloroform
  4. dry with materialThe combined organic extracts are dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe residue is chromatographed over silica gel using
  7. additiona mixture of methylene chloride and methanol (99:1)
  8. washfor the elution
  9. customRecrystallization from diisopropyl ether and methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-dc9d14fa26ed4c2394e5a1296774d9c6
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04336380

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