Hydrochloric Acid → HCID 178421814, Verbindung

HRID 1432804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432804
[CH3:1][C:2]1([CH3:13])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]#[N:12].[N-:14]=[N+:15]=[N-:16].[Na+].Cl>O1CCOCC1.[Br-].[Br-].[Zn+2]>[CH3:1][C:2]1([CH3:13])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]1[N:14]=[N:15][NH:16][N:12]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 178421815(+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile

Produkt 1

HCID 178421814HCID 178421814, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10421208Zinc bromideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

(±)-1,1-Dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile (0.184 g, 1.06 mmol) was taken up in 1,4-dioxane (10 mL) with zinc dibromide (0.500 g, 2.22 mmol) and sodium azide (0.300 g, 4.62 mmol) in a heavy walled glass tube. The resulting solution was heated under microwave irradiation to 200° C. for 1 hour. The solution was poured into 1M aqueous hydrochloric acid (10 mL) and extracted into ethyl acetate (50 mL). Solvent was removed under reduced pressure and the resulting oil purified by preparative HPLC to give (±)-1,1-dimethyl-4-(2H-tetrazol-5-yl)-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene as a white solid. m/z (ES+): 217 [M+H]+, 189 [M−N2+H]+; 1H NMR (CD3OD): δ 2.87 (dd, 1H, J1=16.5, J2=5.6), 2.67 (dd, 1H, J1=16.5, J2=0.8), 2.1-2.0 (m, 2H), 1.08 (s, 3H), 0.69 (s, 3H).

Aufarbeitung

  1. extractionextracted into ethyl acetate (50 mL)
  2. customSolvent was removed under reduced pressure
  3. customthe resulting oil purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cc060f2cc9b84753ba137980303ed6f2
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612106B2

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