2-Hydroxy-5-nitrobenzoyl chloride → HCID 178522691, Verbindung

HRID 614810

Reaktionsgleichung

Reaktionsgleichung von HRID 614810
[N+:1]([C:4]1[CH:12]=[C:8]([C:9](Cl)=[O:10])[C:7]([OH:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:14][C:15]1[NH:19][N:18]=[N:17][N:16]=1>C1(C)C=CC=CC=1>[OH:13][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][C:8]=1[C:9]([NH:14][C:15]1[NH:19][N:18]=[N:17][N:16]=1)=[O:10]

Komponenten

4

Edukt 2

HCID 123739092-Hydroxy-5-nitrobenzoyl chlorideHCID 178509299HCID 178509299, Verbindung

Produkt 1

HCID 178522691HCID 178522691, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

The 5-nitrosalicyloyl chloride thus obtained was dissolved in dry toluene (40 ml) and treated with anhydrous 5-aminotetrazole (3.4 g) and the mixture was stirred and heated at reflux for 12 hours. The mixture was then allowed to cool and was treated with petroleum ether (b.p. 40°-60° C.; 40 ml). The resulting solid was filtered off, washed with petroleum ether (b.p. 40°-60° C.) and stirred with hydrochloric acid (2N; 100 ml). The undissolved solid was filtered off, washed with hydrochloric acid (2N) and with water, and was then dried and dissolved in glacial acetic acid (750 ml). The solution was filtered hot and was then concentrated to 150 ml volume and was then cooled and filtered to give 2-hydroxy-5-nitro-N-(tetrazol-5-yl)-benzamide (2.2 g), m.p. 271°-272° C. (with decomposition).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 12 hours
  3. temperatureto cool
  4. filtrationThe resulting solid was filtered off
  5. washwashed with petroleum ether (b.p. 40°-60° C.)
  6. stirringstirred with hydrochloric acid (2N; 100 ml)
  7. filtrationThe undissolved solid was filtered off
  8. washwashed with hydrochloric acid (2N) and with water
  9. customwas then dried
  10. dissolutiondissolved in glacial acetic acid (750 ml)
  11. filtrationThe solution was filtered hot
  12. concentrationwas then concentrated to 150 ml volume
  13. temperaturewas then cooled
  14. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-bc960eef39e3493d84a57cd5ceff3adc
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04146631

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