Phosphorus oxychloride → 5-Chlorotetrazolo(1,5-a][1,7]naphthyridine

HRID 352476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 352476
[N:1]1[N:5]2[C:6]3[C:11]([C:12](O)=[CH:13][C:4]2=[N:3][N:2]=1)=[CH:10][CH:9]=[N:8][CH:7]=3.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:12]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[N:5]2[N:1]=[N:2][N:3]=[C:4]2[CH:13]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178515416HCID 178515416, Verbindung

Produkt 1

HCID 120158005-Chlorotetrazolo(1,5-a][1,7]naphthyridine

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A suspension of tetrazolo[1,5-a][1,7]naphthyridin-5-ol (3.5 g) in phosphorous oxychloride (15 mL) was heated at 90° C. for 2 hours. The reaction mixture was concentrated under vacuum. The residue was poured into ice water, dichloromethane was added followed by the addition of 10% sodium hydroxide to neutral pH. The product was partitioned into dichloromethane. The dichloromethane layer was separated, dried over magnesium sulfate then concentrated under vacuum to provide 3.8 g of 5-chlorotetrazolo[1,5-a][1,7]naphthyridine as a solid, m.p. 176-177° C. Analysis: Calculated for C8H4ClN5: %C, 46.73; %H, 1.96; %N, 34.06; Found: %C, 46.80; %H, 2.16; %N, 34.45.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionThe residue was poured into ice water, dichloromethane
  3. additionwas added
  4. additionfollowed by the addition of 10% sodium hydroxide to neutral pH
  5. customThe product was partitioned into dichloromethane
  6. customThe dichloromethane layer was separated
  7. dry with materialdried over magnesium sulfate
  8. concentrationthen concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-521bb697f3184b4d9790572c7f1bdb24
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06747040B2

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