Ammonia → HCID 59312283, Verbindung

HRID 2077054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2077054
[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]2[C:15](Cl)=[N:16][C:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)=[N:18][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N>O1CCCC1.[Zn]>[CH2:1]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[N:16][C:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=3)=[N:18][C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 59312360HCID 59312360, Verbindung

Produkt 1

HCID 59312283HCID 59312283, VerbindungAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Zinc dust (943 mg, 14.4 mmol) was added to a mixture of the product from Step B (221 mg, 0.56 mmol) and 0.880 ammonia (20 ml) in tetrahydrofuran (5 ml). This was heated to reflux for 5 h. The reaction mixture was filtered then filtrate was extracted with ethyl acetate (15 ml). The organic phase was dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on a silica cartridge, eluting with DCM:MeOH (100:0 to 95:5), to afford the title compound as a pale orange oil in 66.9% yield, 135 mg.

Aufarbeitung

  1. temperatureThis was heated
  2. temperatureto reflux for 5 h
  3. filtrationThe reaction mixture was filtered
  4. extractionfiltrate was extracted with ethyl acetate (15 ml)
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on a silica cartridge
  8. washeluting with DCM:MeOH (100:0 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-4b70d11b7c804cc581b39dfa2745ddef
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928099B2

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