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Sodium Azide → HCID 86663053, Verbindung

HRID 2410815
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2410815
[NH2:1][C:2]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[N:10][C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N([O-])=O.[Na+].[N-:35]=[N+:36]=[N-].[Na+]>Cl.O>[N:1]([C:2]1[C:11]([C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)=[N:10][C:9]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[N+:35]=[N-:36]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 66599487HCID 66599487, Verbindung

Produkt 1

HCID 86663053HCID 86663053, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel
HCID 962
Water
Lösungsmittel
2×

Versuchsvorschrift

A mixture of methyl 3-amino-2-(4-nitrophenyl)-6-(3-(trifluoromethyl)phenyl)isonicotinate (1 g, 2 4 mmol) in concentrated hydrochloric acid (20 mL, 37%) was cooled in an ice bath and a solution of sodium nitrite (0.99 g, 14.4 mmol) in water (0.5 ml) was added in small portions. The orange-red solution was stirred for 20 min and then a solution of sodium azide (0.94 g, 14.4 mmol) in water (0.5 mL) was added in portions. A precipitate formed and, after 30 min, the reaction was partitioned between DCM and water. The organic phase was washed with brine (2×50 mL), sat. aq. Na2CO3 solution, water, brine and then dried with sodium sulfate. Removal of the solvent followed by silica gel chromatography (elution with 40% EtOAc in hexane) afforded methyl 3-azido-2-(4-nitrophenyl)-6-(3-(trifluoromethyl)phenyl)-isonicotinate (1.0 g, 2 1 mmol, 89% yield). 1H NMR (500 MHz, chloroform-d) δ ppm 8.40 (2H, d, J=9.2), 8.33 (s, 1H), 8.29 (d, 1H, J=8.3), 8.22 (s, 1H), 8.07 (d, 2H, J=8.9), 7.74 (d, 1H, J=7.3), 7.66 (t, 1H, J=7.6), 4.12 (3H, s).

Aufarbeitung

  1. temperaturewas cooled in an ice bath
  2. customA precipitate formed and, after 30 min
  3. customthe reaction was partitioned between DCM and water
  4. washThe organic phase was washed with brine (2×50 mL), sat. aq. Na2CO3 solution, water, brine
  5. dry with materialdried with sodium sulfate
  6. customRemoval of the solvent
  7. washfollowed by silica gel chromatography (elution with 40% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3f1b6f9663db4845aabc3ecad4e9efde
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08815840B2

Notizen zur Reaktion

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