Azido(trimethyl)stannane → HCID 178418841, Verbindung

HRID 11125

Reaktionsgleichung

Reaktionsgleichung von HRID 11125
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([OH:26])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:27][CH2:28][C:29]#[N:30])[C:10]=2[CH:9]=1.[N:31]([Sn](C)(C)C)=[N+:32]=[N-:33]>C1(C)C=CC=CC=1.CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([OH:26])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:27][CH2:28][C:29]3[NH:33][N:32]=[N:31][N:30]=3)[C:10]=2[CH:9]=1

Komponenten

6

Edukt 2

HCID 5104973Azido(trimethyl)stannane2×HCID 248846973-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6(1H)-yl)propanenitrile

Produkt 1

HCID 178418841HCID 178418841, VerbindungAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21735183Dimethylformamide tolueneLösungsmittel

Versuchsvorschrift

To a solution of nitrile (238) (0.68 g, 1.63 mmol) prepared as described in example 98 in toluene/dimethylformamide (5:1, 120 mL) was added azidotrimethyl tin (0.67 g, 3.26 mmol). The resulting solution was heated at reflux for 24 hours before a further portion of azidotrimethyl tin (0.34 g, 1.63 mmol) was added. After a further 24 hours at reflux the reaction was diluted with water and extraction with ethyl acetate. The organic phase was dried, the drying agent was removed and the solution was concentrated to dryness. Chromatography on silica eluting with ethyl acetatelhexane (3:1) to ethyl acetate/methanol (9:1), followed by crystallization from ethyl acetate/hexane, gave tetrazole (272) (0.54 g, 72%) as an orange powder, mp 230–234° C. (dec). 1H NMR δ [(CD3)2SO] 11.06 (br s, 1H), 9.37 (br s, 1H), 8.36 (d, J=2.4 Hz, 1H), 7.61 (s, 1H), 7.56 (m, 1H), 7.48 (m, 4H), 7.10 (dd, J=8.8, 2.4 Hz, 1H), 4.82 (t, J=6.9 Hz, 2H), 3.32 (obscured t, J=6.9 Hz, 2H). Found: C, 52.69; H, 4.05; N, 15.91. C23H15ClN6O3.31/2H2O requires: C, 52.93; H, 4.25; N, 16.09.

Aufarbeitung

  1. temperatureThe resulting solution was heated
  2. additionwas added
  3. temperatureAfter a further 24 hours at reflux the reaction
  4. customThe organic phase was dried
  5. customthe drying agent was removed
  6. concentrationthe solution was concentrated to dryness
  7. customChromatography on silica eluting with ethyl acetatelhexane (3:1) to ethyl acetate/methanol (9:1), followed by crystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-48da5ed2f8704646a3a54504d181f110
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094798B1

Verknüpfte Notizen

Wird geladen…