Imidazole → (S)-4-(3-iodo-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one

HRID 2102542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2102542
O[CH2:2][C@@H:3]([CH3:17])[CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:42]I>C(Cl)Cl>[I:42][CH2:2][C@@H:3]([CH3:17])[CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:16]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 68908602(S)-4-(3-Hydroxy-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one

Produkt 1

HCID 68908548(S)-4-(3-iodo-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-oneAusbeute 103,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A dry 50 mL r-flask was charged with (S)-4-(3-hydroxy-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one (1.0 g, 4.2 mmol), PPh3 (2.2 g, 8.5 mmol), imidazole (0.58 g, 8.5 mmol) and dissolved with CH2Cl2 (25 mL). Iodine (2.2 g, 8.4 mmol) was then added in small portions over 4 h period. After the last addition the reaction was poured onto SiO2 and filtered. Concentration under reduced pressure yielded the crude title compound (1.5 g), which was used without further purification.

Aufarbeitung

  1. additionAfter the last addition the reaction
  2. additionwas poured onto SiO2
  3. filtrationfiltered
  4. concentrationConcentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-19b3dbddcd824ed8bc1a9359c6b682ca
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576078B2

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