Aniline → Carbanilide

HRID 400317

Reaktionsgleichung

Reaktionsgleichung von HRID 400317
[C:1]1([N:7]=[N+]=[N-])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C1C[O:48][CH2:47]C1>>[CH:4]1[CH:3]=[CH:2][C:1]([NH:7][C:47]([NH:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:48])=[CH:6][CH:5]=1

Komponenten

5

Edukt 4

HCID 6115AnilineHCID 8028TetrahydrofuranHCID 69319AzidobenzeneHCID 742671,2-Bis(diphenylphosphino)ethane

Produkt 1

HCID 7595Carbanilide

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In a capped vial (1 mL) containing a solution of phenylazide (6.6 mg, 55 μmol) in dry THF (300 μL), was added [RhCl(cod)]2 (0.27 mg, 0.55 μmol), and 1,2-bis(diphenylphosphino)ethane (0.44 mg, 1.1 μmol) and was shaken until the solution was homogeneous. After addition of aniline (10 μL, 110 μmol), the resulting mixture was transferred to the micro-autoclave, which was pre-charged with [11C]CO. The autoclave (250 μL) was heated at 120° C. for 5 min under 35 MPa and the crude product was transferred to a reduced pressure vial. The radioactivity was measured before and after the vial was flushed with N2 (the [11C]CO-trapping efficiency of 82% was determined based on these values). A small amount of crude product was collected and analyzed by the reversed phase HPLC. Yield of product: 82%. The product was identified by HPLC with an added authentic reference compound.

Aufarbeitung

  1. additionwas pre-charged with [11C]CO
  2. customwas flushed with N2 (the [11C]CO-
  3. customA small amount of crude product was collected

Quellen und Nachweise

ORD-Eintrag
ord-ec54f0937fb144ff9a32b4631bb00133
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741261B2

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