Cyanamide → HCID 15239022, Verbindung

HRID 274210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274210
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N+:10]([O-:12])=O)[C:3]=1[NH2:4].[N:13]#[C:14][NH2:15]>C(O)(=O)C.Cl>[NH2:15][C:14]1[N:13]=[N+:10]([O-:12])[C:5]2[CH:6]=[C:7]([CH3:9])[CH:8]=[C:2]([Br:1])[C:3]=2[N:4]=1

Komponenten

5

Edukt 2

HCID 9864CyanamideHCID 27753062-Bromo-4-methyl-6-nitroaniline

Produkt 1

HCID 15239022HCID 15239022, VerbindungAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 313Hydrochloric AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 13.0 g (56.3 mmol) of 2-bromo-4-methyl-6-nitroaniline stirring in a mixture of 25 ml glacial acetic acid and 5 ml of concentrated hydrochloric acid at 80° C., 29.0 g (690.5 mmol) of cyanamide and 25 ml of concentrated hydrochloric acid were added simultaneously, separately, and very slowly. At one point during the addition, a vigorous exotherm occurred and the external heat immediately removed. After the addition, the reaction was heated at reflux for 15 minutes. On cooling to about 50° C., 100 ml of 25% aqueous sodium hydroxide were added dropwise and the mixture heated at reflux 15 minutes. The reaction was cooled to room temperature, the insoluble orange solid filtered and washed with water followed by ethyl acetate to afford 7.4 g of yellow 3-amino-5-bromo-7-methyl-1,2,4-benzotriazine-1-oxide after drying.

Aufarbeitung

  1. additionAt one point during the addition
  2. temperaturethe external heat immediately
  3. customremoved
  4. additionAfter the addition
  5. temperaturethe reaction was heated
  6. temperatureat reflux for 15 minutes
  7. addition100 ml of 25% aqueous sodium hydroxide were added dropwise
  8. temperaturethe mixture heated
  9. temperatureat reflux 15 minutes
  10. temperatureThe reaction was cooled to room temperature
  11. filtrationthe insoluble orange solid filtered
  12. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-c0c43d1f5a4140f0907303c196d1ba75
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389600

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