Diisopropylethylamine → 2-[Methyl-(2-iodo-phenyl)-amino]benzo[d][1,3]oxazin-4-one

HRID 266674

Reaktionsgleichung

Reaktionsgleichung von HRID 266674
CO[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]=[C:12]=[O:13])=[O:4].Cl.[CH3:15][NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[I:23].C(N(CC)C(C)C)(C)C>C1(C)C=CC=CC=1>[CH3:15][N:16]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[I:23])[C:12]1[O:13][C:3](=[O:4])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:11]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 519494Methyl 2-isocyanatobenzoateHCID 457924062-iodo-N-methylaniline hydrochloride

Produkt 1

HCID 106196342-[Methyl-(2-iodo-phenyl)-amino]benzo[d][1,3]oxazin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 2-methoxycarbonylphenyl isocyanate (1.0 g, 5.6 mmol), N-methyl-2-iodoaniline, hydrochloride (1.6 g, 5.9 mmol) and N,N-diisopropylethylamine (1.1 mL, 6.3 mmol) in 100 mL of toluene was refluxed under N2 for 72 hours. The sample was concentrated, and partitioned between chloroform and 10% HCl. The chloroform was dried (MgSO4), filtered, concentrated and chromatographed (silica gel, methylene chloride) to give the title compound as a yellow solid, mp 144°-148° C.

Aufarbeitung

  1. concentrationThe sample was concentrated
  2. custompartitioned between chloroform and 10% HCl
  3. dry with materialThe chloroform was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed (silica gel, methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-8d09e22f28194e54908f64867acc5346
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05652237

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