Tetrahydrofuran → HCID 58479601, Verbindung

HRID 1516999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516999
[N:1]([C:4]1[C:5]([Cl:11])=[N:6][CH:7]=[CH:8][C:9]=1[I:10])=[N+]=[N-].[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1COCC1.[N-]=[N+]=[N-]>O>[Cl:11][C:5]1[C:4]([N:1]=[P:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:9]([I:10])[CH:8]=[CH:7][N:6]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 33558AzideHCID 149703923-Azido-2-chloro-4-iodopyridine

Produkt 1

HCID 58479601HCID 58479601, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

3-azido-2-chloro-4-iodopyridine (7 g, 25 mmol) and triphenylphosphine (8.5 g, 32 mmol) was stirred in 100 mL 1:1 mixture of THF and water until azide starting material disappears in TLC. After that most of the THF was removed under vacuum. Crude product was partitioned between brine and ethylacetate. Organic layer was isolated, dried over anhd. Na2SO4 and purified by silica gel column chromatography using 5-40% ethyl acetate and hexanes as eluent. 2-chloro-4-iodo-N-(triphenylphosphoranylidene)pyridin-3-amine (12 g, 23 mmol, 93% yield) was isolated as crystalline white solid.

Aufarbeitung

  1. customAfter that most of the THF was removed under vacuum
  2. customCrude product was partitioned between brine and ethylacetate
  3. customOrganic layer was isolated
  4. customdried over anhd
  5. customNa2SO4 and purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3730f77377aa46a48bedceaedafdcddf
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227801B2

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