Hydrochloric Acid → 5-(3-nitrophenyl)tetrazole

HRID 1588028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588028
[C:1]([C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].Cl.C(N(CC)CC)C.[N-:20]=[N+:21]=[N-:22].[Na+].Cl>CN1CCCC1=O>[N+:9]([C:5]1[CH:4]=[C:3]([C:1]2[NH:22][N:21]=[N:20][N:2]=2)[CH:8]=[CH:7][CH:6]=1)([O-:11])=[O:10]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11130Triethylamine hydrochlorideHCID 120793-NitrobenzonitrileHCID 33557Sodium Azide

Produkt 1

HCID 2851295-(3-nitrophenyl)tetrazoleAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a solution of 3-cyanonitrobenzene (20 g, 0.13 mol) in 1-methyl-2-pyrrolidinone (200 mL) was added triethylamine hydrochloride (27.9 g, 0.20 mol) followed by sodium azide (26.4 g, 0.40 mol). The mixture was heated at 160° C. for 1.5 hours, then cooled to ambient temperature, poured into ice water (1000 mL) and acidified using 5M HCl. The solid which precipitated from the mixture was filtered, washed with water and dried under vacuum at 50° C. to afford the title tetrazole (22.1 g, 86%) as a beige powder; mp 154°-156° C. 1H NMR (CDCl3) δ7.59 (1H, dd, J=8 Hz), 8.19 (1H, d, J=8 Hz), 8.36 (1H, d, J=8 Hz), 8.86 (1H, s).

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. customThe solid which precipitated from the mixture
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried under vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-2b90671aace143fbb0b72894e6237651
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05220018

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